Hydrogenated and partially hydrogenated heat-bodied oils and uses thereof

ABSTRACT

The present disclosure presents materials comprising hydrogenated and/or partially hydrogenated polymerized vegetable oils. Non-limiting applications of the polymerized oils, including coatings, binders, blends, and greases are presented. Methods for forming these materials are also disclosed.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a Continuation of U.S. Non-Provisional applicationSer. No. 11/708,998, which is a Continuation-in-Part of U.S.Non-Provisional application Ser. No. 10/428,146, which claims benefitunder 35 U.S.C. §119(e) to U.S. Provisional Applications: 60/376,807,filed May 2, 2002, 60/403,505, filed Aug. 15, 2002, and 60/434,419,filed Dec. 19, 2002, all of which are hereby incorporated herein byreference in their entirety.

BACKGROUND

1. Technical Field

Polymerized biologically-derived oils (“heat-bodied oils”), blownbiologically-derived oils (“heavy bodied blown oils”), vegetable-basedcopolymer oils, and vegetable oil/vegetable-based copolymer oil blendsfor various uses, such as, to make a semi-crystalline wax-like materialare disclosed.

2. Background Art

Petrolatums and micro-crystalline waxes are components in a large numberof products ranging from personal consumer goods to industriallubricants. Petrolatums and micro-crystalline waxes are derived frompetroleum. Thus, the supply of such ubiquitous raw materials isnon-renewable. Petrolatums are semisolid mixtures of hydrocarbons, andare neutral, unctuous, odorless, and tasteless. They have applicationsin the formulation of products such as creams, lotions, hairpreparations, cosmetics, candles, ointments, lubricants and coatings.Typical petrolatums have cone penetration of above 100 dmm and less than275 dmm (ASTM D937). The melting range of petrolatums is about 38° C. toabout 60° C. Micro-crystalline wax is a solid mixture of linear,branched and cyclic hydrocarbons derived from petroleum. It is obtainedfrom the heavy lubricating oil fraction derived from crude oil,subsequent to the removal of paraffin wax. Its characteristics closelyresemble those of the natural waxes, including its high melting point,high viscosity, flexibility at low temperatures, and high cohesion andadhesion. Micro-crystalline waxes are usually higher in molecularweight, viscosity and melting point than paraffin wax. Typically,micro-crystalline wax melting points range from 54° C. to about 102° C.They have needle penetration of above 3 dmm and less than 100 dmm (ASTMD1321). Viscosities are higher than 5.75 centistokes at 100° C.

Heat polymerized oils (“polymerized oils”), often referred to as heatbodied oils, are prepared from unsaturated oils. Linseed, safflower andsoybean oils are commonly used as the starting materials for thisprocess. In addition, fish oils are commonly heat polymerized. Dependingon the oil used, the temperature is held between about 288° C. to about316° C. until a product with a desired viscosity is obtained. Longerreaction times are used to reach a higher viscosity product. Theviscosity of polymerized oils is described using a scale with valuesranging from P to Z₉. During the heat-polymerization reaction, theunsaturated triacylglycerols react to form polymers. As polymerizationtakes place, new carbon-carbon bonds are formed between triacylglycerolunits at sites occupied by double bonds in the originaltriacylglycerols. Ester bonds between glycerol and fatty acids in theoriginal triacylglycerols remain intact.

Polymerized oils have some improved properties for paint, coatings andink applications in comparison to unsaturated triacylglycerols. Theseproperties include improved leveling, pigment wetting, and lessyellowing. Typical polymerized oils still contain a high amount ofunsaturation. The iodine value (“IV”) of heat bodied linseed oils rangesfrom approximately 115-150. Polymerized oils are reactive, viscousliquids at room temperature.

Blown oils differ from polymerized oils. Blown linseed oil is preparedby bubbling air through the oil while heating to temperatures of about110° C. During the process, the oil is polymerized and partiallyoxidized.

Vegetable-based copolymer oils such as maleinized and dicyclopentadieneoils are characterized by a fast drying time and water resistance.Blending such copolymer oils with vegetable oils yields oil blends thatalso possess characteristic properties and provides more diversity ofchemical properties. Other attributed properties can include the uniquehardness of a dried coating when such copolymer oils are incorporatedinto paint or coating formulations.

SUMMARY

Various embodiments of the present disclosure provide materialscomprising hydrogenated and/or partially hydrogenated polymerizedvegetable oils.

In one embodiment, the present disclosure provides a material comprisingat least one of a heat bodied oil and a hydrogenated polymerized oil,wherein the material is one of a binder and a coating. In certainembodiments, the material may be a binder selected from the groupconsisting of a hot melt adhesive, a binder for a wood compositematerial, a binder for a feed block, a binder for an agriculturalproduct, an asphalt binder, and a binder for a personal care product. Inother embodiments, the material may be a coating selected from the groupconsisting of a coating for an agricultural product, a packagingcoating, an edible food coating, and a concrete mold release coating.

According to other embodiments, the present disclosure provides a candlewax comprising a hydrogenated polymerized oil and, optionally, at leastone additive. The additive may be selected from the group consisting ofa vegetable oil, an alkyl ester, a perfume, a scent, and a petroleumderivative. Candles formed from the candle wax are also disclosed.

Still other embodiments of the present disclosure provide a polymercomposition comprising a heat bodied oil or a partially hydrogenatedpolymerized oil, wherein at least on remaining carbon-carbon double bondhas been converted to at least one epoxide.

Further embodiments of the present disclosure provide a materialcomprising at least one of a heat bodied oil and a hydrogenatedpolymerized oil and at least one organic material. The organic materialmay be selected from the group consisting of a vegetable based materialand a petrochemical derived material.

Still further embodiments of the present disclosure provide a greasecomprising a hydrogenated polymerized oil and at least one metal salt ofa free fatty acid.

Other embodiments of the present disclosure provide an emulsioncomprising at least one of a heat bodied oil and a hydrogenatedpolymerized oil; and at least one emulsifier. The emulsifier may beselected from the group consisting of xanthan gum, propylene glycolalginate, locust bean gum, maltodextrin, a fatty alcohol ethoxylate, afatty acid ethoxylate, a sorbitan derivative, a polyglycerol ester,lecithin, and combinations of any thereof

BRIEF DESCRIPTION OF THE DRAWINGS

The various embodiments of the present disclosure will be betterunderstood when read with reference to the following figures.

FIG. 1 illustrates a differential scanning calorimetry scan of a productfrom interesterification of one embodiment of the present disclosure.

DETAILED DESCRIPTION

In a first aspect, the present disclosure is directed to a compositioncomprising a hydrogenated polymerized oil. In this aspect, thehydrogenated polymerized oil is derived from an oil selected from thegroup consisting of fish, animal, vegetable, synthetic andgenetically-modified plant oils, and derivatives and mixtures thereof.In one embodiment, the oil is a vegetable oil. In another embodiment,the vegetable oil is selected from the group consisting of high erucicacid rapeseed, soybean, safflower, canola, castor, sunflower and linseedoils. In an embodiment of the first aspect, the hydrogenated polymerizedoil has an iodine value below about 110. In another embodiment, theiodine value is below about 70 and in another embodiment it is belowabout 30. Compositions comprising a hydrogenated polymerized oil includevegetable-based jellies and waxes. Other compositions include, but arenot limited to, creams, lotions, hair preparations, cosmetics, candles,ointments, lubricants and coatings. One embodiment of this aspect of thepresent disclosure is a composition comprising a hydrogenatedpolymerized oil, wherein the hydrogenated polymerized oil replaces orsupplements a petrolatum or micro-crystalline wax material ingredient inthe composition. For example, according to various embodiments, thehydrogenated polymerized oil may replace from 1% to 100% by weight of apetrolatum or micro-crystalline wax material. In this embodiment, anyproduct containing a petrolatum or micro-crystalline wax can bereformulated to comprise a hydrogenated polymerized oil, such ahydrogenated polymerized oil reduces the amount or eliminates entirelythe requirement of a petrolatum or micro-crystalline wax component inthe composition. When such a composition is reformulated in this manner,the composition retains those characteristics attributed to a petrolatumor micro-crystalline wax material, but the composition contains areduced amount or none of these materials.

A composition of the present disclosure can be a semi-solid or wax-likematerial. The state of the composition will depend on the degree ofhydrogenation, which is measured by the IV. The hardness or softness ofthe material may be a result of the level of hydrogenation. Thus, when amaterial having a different consistency is desired, the oil(s)comprising the composition may be hydrogenated fully or partially toyield the desired consistency. Depending on the material's hardness orsoftness preferred, the oil(s) comprising the composition may behydrogenated to the extent desired. Although the physicalcharacteristics of the composition can be determined empirically, the IVvalues of the oil(s) can be used to measure the degree of hydrogenationfor any given embodiment of the present disclosure. The term“hydrogenated” thus encompasses varying degrees of partial and fullhydrogenation. The IV values of the hydrogenated oil(s) claimed hereinwill fall below about 110, in another embodiment below about 70, and instill another embodiment below about 30. Iodine values with these rangesare characteristic of the desired physical nature of the oil(s)comprising the present disclosure. The present disclosure describes avegetable-based composition that possesses characteristics such asCongeal Point (ASTM D938), Drop Melt Viscosity (ASTM D127), KinematicViscosity (ASTM D445), Needle Penetration (ASTM D1321), similar to theproperties of a petrolatum or micro-crystalline wax.

In another embodiment, the present disclosure is directed to a vegetablebased jelly or wax comprising a hydrogenated polymerized vegetable oil,wherein said oil has an iodine value below about 110. In anotherembodiment, the iodine value is below about 70. In still anotherembodiment the iodine value is below about 30. A vegetable based jellyas described herein would be comparable to a petroleum based jelly suchas Vaseline® petroleum jelly. In this embodiment the composition can bea semi-solid or wax-like material at a temperature between about 0° C.to about 100° C. possessing characteristics such as Congeal Point (ASTMD938), Drop Melt Viscosity (ASTM D127), Kinematic Viscosity (ASTM D445),Needle Penetration (ASTM D1321), similar to the properties of apetrolatum or micro-crystalline wax.

In another embodiment, the composition comprising a hydrogenatedpolymerized oil further comprises a fatty acid ester of triglycerol(triglycerol: CA number 56090-54-1). The fatty acid ester of triglycerolcan be a mono-, di-, tri-, tetra-, or penta-ester. In still otherembodiments, the fatty acid ester is behenic acid ester. Such esters canbe added to modify the micro-crystallinity of wax-like solids orotherwise enhance the desired physical characteristics describe above.

In another embodiment, the composition comprising a hydrogenatedpolymerized oil further comprises a fatty acid ester of triglycerol anda refined, bleached and deodorized (RBD) vegetable oil. In such acomposition, it may be desirable that the hydrogenated polymerized oil,the RBD vegetable oil and the fatty acid ester are respectively presentin a range of ratios wherein the final product has the desiredproperties. Such properties may be affected by the relative ratios ofthe above ingredients and can vary depending on the composition'send-use, which are described herein. In certain embodiments, the RBD oilis selected from the group of vegetable oils consisting of high erucicacid rapeseed, soybean, safflower, canola, castor, sunflower and linseedoils. In another embodiment, the hydrogenated polymerized oil is derivedfrom soy oil, the RBD oil is soy oil, and the fatty acid ester isbehenic acid ester. One embodiment of such a composition comprises ahydrogenated polymerized soy oil, the triacylglycerol is soy oil and thefatty acid ester is a behenic acid ester. In any of these embodiments,the ratios of hydrogenated polymerized oil to RBD vegetable oil to fattyacid ester can be modified to yield the desired product consistency inaccord with the final disposition of the product. The respective amountof any of the above primary ingredients can be adjusted from betweenabout 1% to about 98% of the composition. As exemplified herein (Example15), one embodiment comprises hydrogenated polymerized soy oil, RBD soyoil and behenic acid ester respectively present in a ratio of about49:50:1.

In another embodiment, the composition comprising a hydrogenatedpolymerized oil further comprises one or more hydrogenated vegetableoils. The one or more hydrogenated vegetable oils are derived from agroup of vegetable oils consisting of high erucic acid rapeseed,soybean, safflower, canola, castor, sunflower and linseed oils. In oneembodiment, the hydrogenated vegetable oil is derived from high erucicacid rapeseed, soy or castor oil and the hydrogenated polymerized oil isderived from linseed oil.

In yet another embodiment, the one or more hydrogenated vegetable oilsdescribed above are blended to form a first oil mixture, which is thenadmixed with the hydrogenated polymerized oil. The first oil mixture canbe admixed with the hydrogenated polymerized oil at a ratio of betweenabout 1:1 to about 1:100 first oil mixture to hydrogenated polymerizedoil. The ratio can be adjusted accordingly to suit the desired end-useof the composition or as needed for any reason. In certain embodiments,the first oil mixture is a blend of hydrogenated soy oil andhydrogenated high erucic acid rapeseed oil, wherein the ratio ofhydrogenated soy oil to hydrogenated high erucic acid rapeseed oil isabout 1:1. This ratio forms a blend that is useful as a crystalmodifier, but the ratio can be adjusted accordingly to suit the desiredend-use of the composition or as needed for any reason. Such a first oilmixture can be added to any hydrogenated polymerized oil at a ratiodescribed above.

In another embodiment, the composition comprising a hydrogenatedpolymerized oil and one or more hydrogenated vegetable oils furthercomprises a vegetable oil. Such a vegetable oil is selected from thegroup consisting of high erucic acid rapeseed, soybean, safflower,canola, castor, sunflower and linseed oils. In one embodiment, thevegetable oil is sunflower oil. In this embodiment, the hydrogenatedpolymerized oil, one or more hydrogenated vegetable oils and thevegetable oil are respectively present in a range of ratios wherein thefinal product has the desired properties. Such properties may beaffected by the relative ratios of the above ingredients and can varydepending on the composition's end-use, which are described above. In anembodiment exemplified herein (Example 14), the composition comprisesabout 2 parts sunflower oil, 1 part hydrogenated polymerized linseedoil, and 1 part of one or more hydrogenated vegetable oils as a firstoil mixture (described above), wherein, in this instance, the first oilmixture consists essentially of a 1:1 blend of hydrogenated soy oil andhydrogenated high erucic acid rapeseed oil. This product has a physicalconsistency comparable to that of petroleum jelly. In another embodimentexemplified herein (Example 16), the composition comprises about 2 partssunflower oil, 1 part hydrogenated polymerized linseed oil, and 1 partpartially hydrogenated soy oil. This product has a physical consistencycomparable to that of petroleum jelly.

The composition comprising a hydrogenated polymerized oil and one ormore hydrogenated vegetable oils can further comprise a fatty acid esterof triglycerol. The hydrogenated vegetable oil(s) can be blended withsaid fatty acid ester of triglycerol at a ratio of between about 1:1 toabout 100:1 hydrogenated vegetable oil(s) to said fatty acid ester toform a first blend. The ratio of oil and ester in the first blend can beadjusted accordingly to suit the desired end-use of the composition oras needed for any reason. The first blend can be admixed with thehydrogenated polymerized oil at a ratio of between about 1:1 to about100:1 hydrogenated polymerized oil to said first blend to form thecomposition. In this embodiment, the hydrogenated polymerized oil, oneor more hydrogenated vegetable oils and the fatty acid ester arerespectively present in a range of ratios wherein the final product hasthe desired properties. Such properties may be affected by the relativeratios of the above ingredients and can vary depending on thecomposition's end-use, which are described above. In one embodiment, thehydrogenated polymerized oil is derived from linseed or soy oil; thehydrogenated vegetable oil is derived from soy oil; and the fatty acidester is a behenic acid ester. In an embodiment exemplified herein(Example 12), the blend of hydrogenated vegetable oil/fatty acid esterof triglycerol and hydrogenated polymerized oil to form a final ratio ofabout 40:10:50 hydrogenated soy oil, behenic acid ester and polymerizedlinseed oil.

In all aspects, the composition can further comprise a free radicalscavenger or an anti-oxidant, such as, for example, vitamin E, butylatedhydroxytoluene (BHT) or butylated hydroxyanisole (BHA). In certainembodiments, the free radical scavenger or anti-oxidant is vitamin E. Inother embodiments, the free radical scavenger or anti-oxidant is BHT. Inother embodiments, the free radical scavenger or anti-oxidant is BHA.

In another aspect, the composition can comprise one or more hydrogenatedpolymerized vegetable oils, a first oil mixture consisting essentiallyof hydrogenated soy and high erucic acid rapeseed oils, one or morevegetable oils and vitamin E. An embodiment exemplified herein (Example17) comprises a first oil mixture of hydrogenated soy and high erucicacid rapeseed oils at a ratio of about 1:1.

In another embodiment, the present disclosure describes a compositionconsisting essentially of a hydrogenated polymerized oil. Thehydrogenated polymerized oil as described herein has an iodine valuebelow about 110. In certain embodiments, the iodine value is below about70. In other embodiments, the iodine value is below about 30.

In another embodiment, the present disclosure is directed to avegetable-based coating comprising a hydrogenated polymerized vegetableoil having an iodine value below about 110. In one embodiment, theiodine value is below about 70 and in another embodiment below about 30.The vegetable based coating described herein would be useful forpackaging coatings and the like. Such coatings include, but are notlimited to, polyurethane coatings.

In yet another aspect, the present disclosure is directed to a processof preparing a hydrogenated polymerized oil composition. The processcomprises hydrogenating a polymerized oil. In certain embodiments,hydrogenation comprises reacting the oil under a vapor pressure ofhydrogen in the presence of a catalyst. In another embodiment,hydrogenation further comprises:

a) purging a reaction vessel containing a polymerized oil and a catalystwith hydrogen prior to pressurizing with hydrogen,

b) heating the pressurized vessel containing the oil and catalyst to atemperature of between about 150° C. to about 400° C.,

c) adjusting the vapor pressure in the vessel by feeding hydrogen gasinto the heated vessel, and

d) cooling and filtering the product produced in steps a through c.

In certain embodiments, the vapor pressure of hydrogen is between about50 psig to about 1000 psig.

In certain embodiments, the catalyst is selected from the groupconsisting of a nickel-based catalyst, copper, copper-chromite, platinumand palladium.

In another aspect, the present disclosure describes a process whereinthe product is a semi-solid or wax-like material at a temperaturebetween about 0° C. to about 100° C. comprising a hydrogenatedpolymerized oil. Such a material contains a hydrogenated oil with aniodine value below about 110. In one embodiment, the iodine value isbelow about 70 and in another embodiment the iodine value is below about30.

In another embodiment, the present disclosure is directed to a processwherein said polymerized oil is derived from an oil selected from thegroup consisting of fish, animal, vegetable, synthetic andgenetically-modified plant oils, and derivatives and mixtures thereof.In certain embodiments, the oil is a vegetable oil. In variousembodiments, the vegetable oil is selected from the group consisting ofsoybean, safflower, canola, castor, sunflower and linseed oils.

In another aspect, the present disclosure describes a compositioncomprising a hydrogenated blown oil. In this aspect of the presentdisclosure, the hydrogenated blown oil is derived from an oil selectedfrom the group consisting of fish, animal, vegetable, synthetic andgenetically-modified plant oils, and derivatives and mixtures thereof Incertain embodiments, the oil is a vegetable oil. In various embodiments,the vegetable oil is selected from the group consisting of high erucicacid rapeseed, soybean, safflower, canola, castor, sunflower and linseedoils. In an embodiment of the first aspect, the hydrogenated blown oilhas a hydroxyl value below about 150, and an iodine value below about110. In another embodiment, the iodine value is below about 70, and instill another embodiment below about 30. Compositions comprising ahydrogenated blown oil include vegetable-based jellies and waxes. Othercompositions include, but are not limited to, creams, lotions, hairpreparations, cosmetics, candles, ointments, lubricants, binders andcoatings, including but not limited to polyurethane coatings. A oneembodiment of this aspect of the present disclosure is a compositioncomprising a hydrogenated blown oil, wherein the composition replaces orsupplements a petrolatum or micro-crystalline wax material ingredient inthe composition. In this embodiment, any product containing a petrolatumor micro-crystalline wax can be reformulated to comprise a hydrogenatedblown oil, such a hydrogenated blown oil reduces the amount oreliminates entirely the requirement of a petrolatum or micro-crystallinewax component in the composition. When such a composition isreformulated in this manner, the composition retains thosecharacteristics attributed to a petrolatum or micro-crystalline waxmaterial, but the composition contains a reduced amount or none of thesematerials.

In another embodiment, the present disclosure is directed to a vegetablebased jelly or wax comprising a hydrogenated blown vegetable oil,wherein said oil has an iodine value below about 110. In one embodiment,the iodine value is below about 70, and in another embodiment belowabout 30. A vegetable based jelly as described herein would becomparable to a petroleum based jelly such as Vaseline® petroleum jelly.In this embodiment the composition can be a semi-solid or wax-likematerial at a temperature between about 0° C. to about 100° C.possessing characteristics such as Congeal Point (ASTM D938), Drop MeltViscosity (ASTM D127), Kinematic Viscosity (ASTM D445), NeedlePenetration (ASTM D1321), similar to the properties of a petrolatum ormicro-crystalline wax.

In another aspect, the present disclosure describes a compositionconsisting essentially of a hydrogenated blown oil.

In certain embodiments the hydrogenated blown oil is derived from an oilselected from the group consisting of fish, animal, vegetable, syntheticand genetically-modified plant oil, and derivatives and mixturesthereof. In other embodiments, the blown oil is derived from a vegetableoil. In certain embodiments, the vegetable oil is high erucic acidrapeseed, soybean, safflower, canola, castor, sunflower or linseed oil.According to various embodiments, such a hydrogenated blown oil has ahydroxyl value below about 150. In other embodiments, a hydrogenatedblown oil composition has an iodine value below about 110. In stillother embodiments, the iodine value is below about 70 and in otherembodiments below about 30. In one embodiment, the compositionconsisting essentially of a hydrogenated blown oil is a semi-solid orwax-like material at a temperature between about 0° C. to about 100° C.In this embodiment, the disclosure describes a composition thatpossesses characteristics such as Congeal Point (ASTM D938), Drop MeltViscosity (ASTM D127), Kinematic Viscosity (ASTM D445), NeedlePenetration (ASTM D1321), similar to the properties of a petrolatum ormicro-crystalline wax.

In another embodiment, the present disclosure is directed to avegetable-based coating comprising a hydrogenated blown vegetable oil,wherein said oil has an iodine value below about 110. In certainembodiments, the iodine value is below about 70, and in otherembodiments below about 30. The vegetable based coating described hereinwould be useful for packaging coatings and the like.

In another aspect, the present disclosure describes a process forpreparing a hydrogenated blown oil composition. The process compriseshydrogenating a blown oil. In certain embodiments, hydrogenationcomprises reacting the oil under a vapor pressure of hydrogen in thepresence of a catalyst. In another embodiment, hydrogenation furthercomprises:

a) purging a reaction vessel containing a blown oil and a catalyst withhydrogen prior to pressurizing with hydrogen,

b) heating the pressurized vessel containing the oil and catalyst to atemperature of between about 150° C. to about 400° C.,

c) adjusting the vapor pressure in the vessel by feeding hydrogen gasinto the heated vessel, and

d) cooling and filtering the product produced in steps a through c.

In certain embodiments, the vapor pressure of hydrogen is between about50 psig to about 1000 psig.

In certain embodiments, the catalyst is selected from the groupconsisting of a nickel-based catalyst, copper, copper-chromite, platinumand palladium.

In another embodiment, the present disclosure describes a processwherein said hydrogenated blown oil product has a hydroxyl value belowabout 150.

In certain embodiments, the hydrogenated blown oil product has an iodinevalue below about 110. In other embodiments, the iodine value is belowabout 70, and in still other embodiments below about 30.

In one embodiment, the blown oil is derived from an oil selected fromthe group consisting of fish, animal, vegetable, synthetic andgenetically-modified plant oil, and derivatives and mixtures thereof. Inother embodiments, the blown oil is derived from a vegetable oil. Incertain embodiments, the vegetable oil is linseed or soy oil.

In another aspect, the present disclosure describes a compositioncomprising a hydrogenated copolymer oil. In an embodiment of thisaspect, the hydrogenated copolymer oil has an iodine value below about110. In certain embodiments, the iodine value is below about 70, and inother embodiments below about 30. Compositions comprising a hydrogenatedcopolymer oil include vegetable-based jellies and waxes. Othercompositions include, but are not limited to, creams, lotions, hairpreparations, cosmetics, candles, ointments, lubricants, binders, andcoatings. One embodiment of this aspect of the present disclosure is acomposition comprising a hydrogenated copolymer oil, wherein thehydrogenated copolymer oil replaces or supplements a petrolatum ormicro-crystalline wax material ingredient in the composition. In thisembodiment, any product containing a petrolatum or micro-crystalline waxcan be reformulated to comprise a hydrogenated copolymer oil, such ahydrogenated copolymer oil reduces the amount or eliminates entirely therequirement of a petrolatum or micro-crystalline wax component in thecomposition. When such a composition is reformulated in this manner, thecomposition retains those characteristics attributed to a petrolatum ormicro-crystalline wax material, but the composition contains a reducedamount or none of these materials.

In another embodiment, the present disclosure is directed to a vegetablebased jelly or wax comprising a hydrogenated copolymer oil, wherein saidoil has an iodine value below about 110. In certain embodiments, theiodine value is below about 70, and in other embodiments below about 30.A vegetable based jelly as described herein would be comparable to apetroleum based jelly such as Vaseline® petroleum jelly. In thisembodiment the composition can be a semi-solid or wax-like material at atemperature between about 0° C. to about 100° C. possessingcharacteristics such as Congeal Point (ASTM D938), Drop Melt Viscosity(ASTM D127), Kinematic Viscosity (ASTM D445), Needle Penetration (ASTMD1321), similar to the properties of a petrolatum or micro-crystallinewax.

In another embodiment, the present disclosure describes a compositionconsisting essentially of a hydrogenated copolymer oil.

The hydrogenated copolymer oil has an iodine value below about 110. Incertain embodiments, the iodine value is below about 70, and in otherembodiments below about 30. Examples of copolymer oils suitable forhydrogenation include, but are not limited to, dicyclopentadiene andmaleic anhydride/polyol oils. With regard to a copolymer oil possessinghydroxyl moieties, such as a maleic anhydride/polyol oil, the hydroxylvalue of such an oil may be below about 150. In certain embodiments, thecomposition consisting essentially of a hydrogenated copolymer oil is asemi-crystalline wax-like material at a temperature between about 0° C.to about 100° C. In this embodiment, the disclosure describes acomposition that possesses characteristics such as Congeal Point (ASTMD938), Drop Melt Viscosity (ASTM D127), Kinematic Viscosity (ASTM D445),Needle Penetration (ASTM D1321), similar to the properties of apetrolatum or micro-crystalline wax.

In another embodiment, the present disclosure is directed to avegetable-based coating comprising a hydrogenated copolymer oil havingan iodine value below about 110. In certain embodiments, the iodinevalue is below about 70, and in other embodiments below about 30. Thevegetable based coating described herein would be useful for packagingcoatings and the like.

The present disclosure is also directed to a product having similarcharacteristics as a microcrystalline wax or petrolatum product, whereinthe product is formulated using any of the following ingredients in anycombination: one or more neat vegetable oils, one or more hydrogenated(including partially hydrogenated) vegetable oils, one or morehydrogenated (including partially hydrogenated) polymerized oils, one ormore hydrogenated (including partially hydrogenated) blown oils, one ormore hydrogenated (including partially hydrogenated) copolymer oils, afatty acid ester of a triglycerol and an antioxidant.

In another aspect, the present disclosure describes a process forpreparing a hydrogenated copolymer oil composition. The processcomprises hydrogenating a copolymer oil. In certain embodiments,hydrogenation comprises reacting the oil under a vapor pressure ofhydrogen in the presence of a catalyst. In another embodiment,hydrogenation further comprises:

a) purging a reaction vessel containing a copolymer oil and a catalystwith hydrogen prior to pressurizing with hydrogen,

b) heating the pressurized vessel containing the oil and catalyst to atemperature of between about 150° C. to about 400° C.,

c) adjusting the vapor pressure in the vessel by feeding hydrogen gasinto the heated vessel, and

d) cooling and filtering the product produced in steps a through c.

In certain embodiments, the vapor pressure of hydrogen is between about50 psig to about 1000 psig.

In certain embodiments, the catalyst is selected from the groupconsisting of a nickel-based catalyst, copper, copper-chromite, platinumand palladium.

In another embodiment, the present disclosure is directed to a vegetablebased jelly or wax comprising a hydrogenated copolymer/vegetable oilblend, wherein said oil blend has an iodine value below about 110. Incertain embodiments, the iodine value is below about 70, and in anotherembodiment below about 30. A vegetable based jelly as described hereinwould be comparable to a petroleum based jelly such as Vaseline®petroleum jelly. In this embodiment the composition can be a semi-solidor wax-like material at a temperature between about 0° C. to about 100°C. possessing characteristics such as Congeal Point (ASTM D938), DropMelt Viscosity (ASTM D127), Kinematic Viscosity (ASTM D445), NeedlePenetration (ASTM D1321), similar to the properties of a petrolatum ormicro-crystalline wax.

In another aspect, the present disclosure describes a compositionconsisting essentially of a hydrogenated copolymer/vegetable oil blend.In certain embodiments, the composition consisting essentially of ahydrogenated copolymer/vegetable oil blend is a semi-crystallinewax-like material at a temperature between about 0° C. to about 100° C.The hydrogenated copolymer/vegetable oil blend as described herein hasan iodine value below about 110. In certain embodiments, the iodinevalue is below about 70, and in other embodiments below about 30. Inthis embodiment, the disclosure describes a composition that possessescharacteristics such as Congeal Point (ASTM D938), Drop Melt Viscosity(ASTM D127), Kinematic Viscosity (ASTM D445), Needle Penetration (ASTMD1321), similar to the properties of a petrolatum or micro-crystallinewax.

Examples of copolymer oils suitable for blending with a vegetable oilinclude, but are not limited to, dicyclopentadiene and maleicanhydride/polyol oils. Vegetable oils suitable for blending with acopolymer oil include any vegetable derived oil or genetically-modifiedplant oil. In certain embodiments, the vegetable oil in the oil blend issoybean, safflower, canola, castor, sunflower or linseed oil. In otherembodiments, the vegetable oil in the oil blend is linseed oil, and thecopolymer oil is dicyclopentadiene or maleic anhydride/polyol oil.

In another embodiment, the present disclosure is directed to avegetable-based coating comprising a hydrogenated copolymer/vegetableoil blend having an iodine value below about 110. In certainembodiments, the iodine value is below about 70, and in anotherembodiment below about 30. The vegetable based coating described hereinwould be useful for packaging coatings and the like.

In another aspect, the present disclosure describes a process forpreparing a hydrogenated copolymer/vegetable oil composition. Theprocess comprises hydrogenating a copolymer/vegetable oil. In certainembodiments, hydrogenation comprises reacting the oil under a vaporpressure of hydrogen in the presence of a catalyst. In anotherembodiment, hydrogenation further comprises:

a) purging a reaction vessel containing a copolymer/vegetable oil and acatalyst with hydrogen prior to pressurizing with hydrogen,

b) heating the pressurized vessel containing the oil and catalyst to atemperature of between about 150° C. to about 400° C.,

c) adjusting the vapor pressure in the vessel by feeding hydrogen gasinto the heated vessel, and

d) cooling and filtering the product produced in steps a through c.

In certain embodiments, the vapor pressure of hydrogen is between about50 psig to about 1000 psig.

In certain embodiments, the catalyst is selected from the groupconsisting of a nickel-based catalyst, copper, copper-chromite, platinumand palladium.

In certain embodiments, the hydrogenated copolymer/vegetable oil producthas an iodine value below about 110. In other embodiments, the iodinevalue is below about 70, and in still another embodiment below about 30.

It has been discovered that hydrogenation of the carbon-carbon doublebonds in polymerized, blown, copolymer and copolymer/vegetable blendoils increases the solidification point, improves oxidative stability,decreases reactivity and increases crystallinity. It has further beenfound that such hydrogenated oil compositions display properties similarto petrolatums and micro-crystalline waxes. If only partialhydrogenation of such an oil is carried out, a chemically reactivesemi-solid or wax-like material is produced. Partially hydrogenated oilsare capable of forming cross-linked network structures. Other materialssuch as neat vegetable oils, hydrogenated vegetable oils, oil blends,polyglycerol esters and hydrogenated triacylglycerols can be blendedwith the hydrogenated oils to further modify physical properties asdesired.

It has also been discovered that blown oils or copolymer oils containingfree hydroxyl moieties can be hydrogenated to yield a product similar topetrolatums and micro-crystalline waxes, or useful in coatings,including but not limited to urethane coatings. Such hydrogenated oilshave hydroxyl values below about 150. The hydroxyl moieties can beuseful sites for further chemical modifications of the presentdisclosure.

High erucic acid rapeseed oil (HEAR) is a type of rapeseed oil typicallycontaining between 40 and 50% erucic acid.

Fatty acids are composed of a carboxylic acid attached to an alkylchain. The alkyl chain may be saturated or unsaturated, and branched,cyclic or straight.

The term “genetically-modified plant oils” refers to an oil derived froma crop source that has been genetically altered or manipulated by achemical, biological or recombinant technological process, wherein aftersuch a process the genetic material of the crop source is modified.

Examples to demonstrate some of the properties of the compositions ofthe present disclosure are described herein. Iodine Value is the numberof centigrams of iodine absorbed under standard conditions by 1 gram offat. It is a measure of the average degree of unsaturation. Hydroxylvalue is defined as the milligrams of potassium hydroxide equivalent tothe hydroxy content in 1 gram of sample material.

Material based on heat-bodied and/or polymerized oils, includingdehydrated oils, oils reacted with copolymers, blown oils, maleictreated oils, and reconstituted oils, may be hydrogenated, includingpartial hydrogenation, as described herein, to provide materialssuitable for various commercial applications as described herein. Forexample, according to certain embodiments, the heat-bodied oils andpolymerized oils described herein may be at least partially hydrogenatedto provide materials that may be used as a binder material or as acoating material. In other embodiments, the heat-bodied oils and/orpolymerized oils, which may or may not be at least partiallyhydrogenated, may be blended with other biobased material and/orpetrochemical derived materials to make compositions as describedherein.

As used herein, the term “bioderived” means derived from or synthesizedby a renewable biological feedstock, such as, for example, anagricultural, forestry, plant, bacterial, or animal feedstock. As usedherein, the term “bio-based” means a product that is composed, in wholeor in significant part, of biological products or renewable agriculturalmaterials (including plant, animal and marine materials) or forestrymaterials. As used herein, the term “petroleum derived” means a productderived from or synthesized from petroleum or a petrochemical feedstock.

According to certain embodiments, polymerized vegetable oils, asdescribed herein, including at least partially hydrogenated polymerizedvegetable oils, may be blended with other biobased materials.Non-limiting examples of biobased materials, including materials derivedfrom plant or animal sources, which may be mixed with the polymerizedoils of the present disclosure include propylene glycol monoesters(“PGMEs”), monoacylglycerols, diacylglycerols, mixtures ofmonoacylglycerols and diacylglycerols, esters of dianhydrohexitols,methyl esters, hydrogenated methyl esters, esters of polyols (includingsorbitol and sorbitan), ethoxylated fatty acid derivatives, stanols,sterols (such as plant sterols, including soy sterols), stanyl esters,steryl esters, polyglycerol esters, and combinations of any thereof.

For example, according to certain embodiments, the at least partiallyhydrogenated polymerized oils may be blended with biobased esters, suchas, PGMEs. Non-limiting examples of bio-based PGMEs include PGMEs offatty acids (organic carboxylic acids having from 10-22 carbon atoms inthe main chain), such as propylene glycol monostearate, propylene glycolmonooleate, propylene glycol monoelaidate, propylene glycolmonopalmitate, propylene glycol monomyristate, propylene glycolmonolaurate, propylene glycol monolinoleate, propylene glycolmonolinolenate, propylene glycol monobehenate, propylene glycolmonoerucate, and combinations of any thereof. Various suitable PGMEshave high melting points and good hardness, such that when they areblended with petrolatum-like hydrogenated polymerized oil material mayresult in a blended material having good hardness, melting point,flexibility and tackiness that may be suitable for an adhesive or abinder material. For example, certain blends of hydrogenated polymerizedoils and PGMEs, such as a propylene glycol monostearate, for example ablend comprising from 30% to 70% hydrogenated polymerized oil and 70% to30% of PGME, may have good hardness, with melting points in the range of40° C. to 50° C., and a suitable degree of tackiness for use as anadhesive. According to other embodiments where a high melting point maybe desired, other high melting point biobased vegetable oil derivatives,such as, for example, hydrogenated castor oil, hydrogenated high erucicacid rapeseed oil (“HEAR”), and the like, may be added to the blend togive higher melting points (about 86° C. for added hydrogenated castoroil and about 71° C. for added hydrogenated HEAR oil). According toother embodiments, the blend of at least partially hydrogenatedpolymerized oils and biobased esters may comprise stanols or sterols,such as, high melting point stanols or sterols (including but notlimited to stanols or sterols with a melting point from about 130° C. to150° C.). One non-limiting example of a plant sterol includes sitosterolfrom soybeans which has a melting point of 136° C.-140° C. Blendscomprising at least partially hydrogenated polymerized oils and soy orplant stanols or plant sterols (such as sitosterol) may have meltingpoints exceeding 140° C. While not intending to be limited by anyinterpretation, the high melting point components may help network therest of the wax mixture up to or near their melting point. For example,the plant sterol and/or plant stanol may act as a nucleating agent toseed crystallization in a crystalline wax-like product.

In other embodiments where a lower melting point may be desired, the atleast partially hydrogenated polymerized oil may be blended with a lowmelting point bio-based vegetable oil derivative, such as, but notlimited to, a stanyl ester and/or a steryl ester. Since stanyl estersand steryl esters have low melting points (approx. 30° C. to 50° C.),the resulting blend may have lower melting characteristics.

According to other embodiments, the at least partially hydrogenatedpolymerized oils may be blended with petrochemical derived materials.For example, according to certain embodiments, the at least partiallyhydrogenated polymerized oil may be blended with petrochemical derivedmaterials, such as, for example, paraffin waxes, microcrystalline waxes,mineral oils, and combinations of any thereof. Petroleum basedmaterials, such as, paraffin waxes, microcrystalline waxes, mineraloils, and the like, are generally non-polar and miscible with the atleast partially hydrogenated polymerized oils of the present disclosure.For example, according to certain embodiments, mixtures and blends ofthe at least partially hydrogenated polymerized oil and the petroleumbased materials may be produced by melting the components, mixing themelted components to give a solution, and allowing the blend or mixtureto cool. The blends and mixtures may then be used for variousapplications as described herein. Forming a blend of the bio-based atleast partially hydrogenated polymerized oils and the petroleum basedmaterials may allow for the at least partial replacement ofnon-renewable petroleum based materials with renewable bio-basedmaterials. According to one non-limiting example, a blend comprisingfrom 30% to 70% hydrogenated polymerized oil and 70% to 30% of apetroleum based material, such as paraffin wax, microcrystalline waxes,and mineral oils, may be used in a variety of applications, such as acoating, as described herein.

Bio-based content of a product may be verified by ASTM InternationalRadioisotope Standard Method D 6866. ASTM International RadioisotopeStandard Method D 6866 determines bio-based content of a material basedon the amount of bio-based carbon in the material or product as apercent of the weight (mass) of the total organic carbon in the materialor product. Both bio-derived and bio-based products will have a carbonisotope ratio characteristic of a biologically derived composition.These methods require the measurement of variations in isotopicabundance between bio-based products and petroleum derived products, forexample, by liquid scintillation counting, accelerator massspectrometry, or high precision isotope ratio mass spectrometry.Isotopic ratios of the isotopes of carbon, such as the ¹³C/¹²C carbonisotopic ratio or the ⁴C/¹²C carbon isotopic ratio, can be determinedusing analytical methods, such as isotope ratio mass spectrometry, witha high degree of precision. Studies have shown that isotopicfractionation due to physiological processes, such as, for example, CO₂transport within plants during photosynthesis, leads to specificisotopic ratios in natural or bioderived compounds. Petroleum andpetroleum derived products have a different ¹³C/¹²C carbon isotopicratio due to different chemical processes and isotopic fractionationduring the generation of petroleum. In addition, radioactive decay ofthe unstable ¹⁴C carbon radioisotope leads to different isotope ratiosin bio-based products compared to petroleum products. Thus, bio-basedproducts may be differentiated from petroleum derived products.

The materials, according to various embodiments of the presentdisclosure, may comprise at least one of a heat bodied oil and an atleast partially hydrogenated polymerized oil. The materials may be usedas a binder. For example, according to certain embodiments, the materialmay be a binder, such as a hot melt adhesive, a binder for a woodcomposite material, a binder for a feed block, a binder for anagricultural product, an asphalt binder, or a binder for a personal careproduct. Various embodiments of the binders are discussed herein.

According to various embodiments of the present disclosure, the at leastpartially hydrogenated polymerized oil may be blended with a vegetableoil product, such as, for example, soybean oil, to provide a waxsuitable for use in various applications, such as, for example, acandle, a fireplace log, or a fire starting composition. According toother embodiments, other bio-based esters, as described herein, may beadded to the blend to modify the characteristics of the candle. Forexample, addition of hydrogenated vegetable oil, sterols, stanols,steryl esters, stanyl esters, and/or PGMEs may result in candle waxhaving modified characteristics, such as, increased hardness, changes intexture, and changes in morphology. According to other embodiments, theat least partially hydrogenated polymerized oils of the presentdisclosure may be blended with petroleum based materials, such as,paraffin wax, microcrystalline waxes, mineral oils, and the like, toform a wax material that may be used as a candle wax. The materials ofthe present disclosure may be mixed with a biologically derived oilproduct, a petroleum derived wax, or any combinations of these at anydesired amount ranging from an intentionally incorporated trace, such asabout 0.01 percent by weight to 100 percent by weight.

According to other embodiments, the at least partially hydrogenatedpolymerized oils of the present disclosure may be interesterified withtriacylglycerol oils, for example, vegetable oils, which may benon-hydrogenated, partially hydrogenated, and fully hydrogenated. Asused herein, the terms “interesterified” and “interesterification” referto a chemical reaction in which the ester functional groups in the twoor more components exchange the acyl portion of the at least one of theesters of triacylglycerols in vegetable oils (including hydrogenated andpolymerized vegetable oils), as shown in equation 1.

For example, the hydrogenated heat-bodied or polymerized oils of thepresent disclosure may be interesterified with hydrogenated HEAR oil toproduce a composition having a high monoester content. Suitableprocedures for interesterification include, but are not limited to,those described in U.S. Pat. Nos. 2,442,531, 2,442,532, and 6,723,863,the disclosures of each of which are incorporated by reference herein intheir entirety, including enzymatic interesterification, acid mediatedinteresterification, and base mediated interesterification. According tocertain embodiments, interesterification of the at least partiallyhydrogenated heat-bodied or polymerized oil with other vegetable oils,such as hydrogenated HEAR oil may be used to produce a microcrystallinewax material. The microcrystalline wax material may be composed ofprimarily bio-based products.

According to other embodiments, one or more carbon-carbon double bondsin the molecular structure of the polymerized oils and partiallyhydrogenated polymerized oils of the present disclosure may be subjectedto epoxidation. Epoxidation, either by a chemical epoxidation or anenzymatic epoxidation, converts the one or more carbon-carbon doublebonds on the polymerized oil to an epoxide. According to variousembodiments, at least one up to all of the remaining carbon-carbondouble bonds of the polymerized oil may be converted to epoxides. Theresulting epoxy systems may react with nucleophiles, such asamines/polyamides and hydroxyls. In other embodiments, the epoxidizedpolymerized oils may be used as acid scavengers (such as HCl scavengers)or as plasticizers, lubricants, or additives in PVC or other plasticcompounding application.

According to other embodiments, the at least partially hydrogenatedpolymerized oils of the present disclosure may be utilized in adhesiveapplications, such as, hot melt adhesive applications. For example, atleast partially hydrogenated polymerized vegetable oils, such as soybeanoil, may be used as a substitute for at least a portion of the petroleumwaxes used in the manufacture of hot melt adhesives.

Waxes that are to be used in hot melt adhesives must have a relativelysharp melt point to yield an adhesive with a short “set speed” andcontrollable open time. As used herein, the term “sharp melt point”means the hot melt adhesive melts over a narrow temperature range. Asused herein, the term phrase “short set speed” means the hot meltadhesive sets or hardens over a short period of time. As used herein,the term phrase “open time” means the time a hot melt adhesive takes tosolidify to a point where it can no longer bond with the intendedarticle. The melt point is another property in addition tocompatibility. The wax must also allow for a reduction of overalladhesive viscosity to allow for the proper application or coating of thehot melt adhesive on the intended surface. Generally, hot melt adhesiveformulations are heated to 148° C. to 177° C. prior to application inorder to reduce viscosity. The wax must be stable at these temperaturesto allow for extended periods as a molten product prior to application.Other components, such as, but not limited to, antioxidants (forexample, hindered phenols) and free radical scavengers (for example, butnot limited to, butylated hydroxy toluene (“BHT”), butylated hydroxyanisole (“BHA”), and Irganox 1010 (commercially available from CibaCorp., Tarrytown, N.Y.)) may be added to the adhesive compound tofurther enhance thermal stability.

For example, according to certain embodiments, the present disclosureprovides for a material comprising at least one of a heat bodied oil anda hydrogenated polymerized oil wherein the material is a binder such asa hot melt adhesive. The hot melt adhesive may comprise from 40% to 50%by weight of the at least partially hydrogenated polymerized oil, 40% to50% by weight of a hydrocarbon resin, and 10% to 20% of a hydrogenatedvegetable oil, such as, but not limited to, a hydrogenated soybean oilor a hydrogenated oil selected from the following: butterfat, cocoabutter, cocoa butter substitutes, illipe fat, kokum butter, milk fat,mowrah fat, phulwara butter, sal fat, shea fat, borneo tallow, lard,lanolin, beef tallow, mutton tallow, tallow, animal fat, camelina oil,canola oil, castor oil, coconut oil, coriander oil, corn oil, cottonseedoil, hazelnut oil, hempseed oil, jatropha oil, linseed oil, mango kerneloil, meadowfoam oil, mustard oil, neat's foot oil, olive oil, palm oil,palm kernel oil, peanut oil, rapeseed oil, rice bran oil, safflower oil,sasanqua oil, shea butter, soybean oil, sunflower seed oil, tall oil,tsubaki oil, tung oil, vegetable oils, marine oils, menhaden oil,candlefish oil, cod-liver oil, orange roughy oil, pile herd oil, sardineoil, whale oils, herring oils, triacylglycerols, diacylglycerols,monoacylglycerols, triolein, palm olein, palm stearin, palm kernelolein, palm kernel stearin, triacylglycerols of medium chain fattyacids, and derivatives, conjugated derivatives, genetically-modifiedderivatives and mixtures thereof. According to certain embodiments ofthe hot melt adhesive, wherein the hydrogenated polymerized oil is apartially hydrogenated polymerized oil, the partially hydrogenatedpolymerized oil in the binder may undergo an oxidative curing. Accordingto certain embodiments wherein the partially hydrogenated polymerizedoil undergoes an oxidative curing, the hot melt adhesive may be athermosetting resin that thermosets during the curing and will notre-melt upon reheating. According to the various embodiments, the atleast partially hydrogenated polymerized oils may act as a tackifier inthe hot melt application and also may impart both flexibility and goodlow-temperature adhesion to the adhesive.

According to other embodiments, the at least partially hydrogenatedpolymerized oils of the present disclosure may be used as part of abinder for wood composite applications. For example, the materialsaccording to certain embodiments of the present disclosure may be abinder for a wood composite material. In one embodiment, the binder maybe applied in a molten form (that is, the molten binder material may bemelted and mixed with the wood composite materials) and then molded intothe final product and set upon cooling. In another embodiment, thebinder may be applied in the form of an emulsion, that is, the emulsioncomprising the binder material may be mixed with the wood compositematerials, and the mixture molded into the final product. Further,according to certain embodiments, the partially hydrogenated polymerizedoils in the binders may be crosslinked after formation of the woodcomposite product, for example by oxidative curing to form crosslinksbetween double bonds in the polymerized oil. The resulting crosslinkedpolymerized oil binder system may be more rigid than the non-crosslinkedpolymerized oil binder and may impart additional dimensional stabilityto the wood composite product. The addition rate of the at leastpartially hydrogenated polymerized oils of the present disclosure mayvary from 0.5% to 50% by weight. The lower limit of addition canalternatively be 1%, 1.25%, 2%, 2.5%, 3%, 4%, or 5% by wood weight, onthe same basis. The upper limit of addition can alternatively be 50%,40%, 30%, 25%, 20%, 15%, 14%, 13%, 12%, 11%, 10%, 8%, 6%, or 5% by woodweight, on the same basis. In comparison to the use of non-polymerizedvegetable oils as wood composite binders, the wood composite bindermaterials of the present disclosure offer higher molecular weightderivatives. For example, partially hydrogenated polymerized oil, forexample with and IV of 50 or more will polymerized under oxidativecuring to form a cross linked network with a large molecular weight. Itis believed that less curing is required to reach the gel point with thepolymerized oils than with triacylglycerol oils, which have a loweraverage molecular weight than polymerized oils, including partiallyhydrogenated polymerized oils. In other embodiments, the bindercomprising the at least partially hydrogenated polymerized oil may alsoimpart moisture resistance to the wood composite product by forming anat least partially moisture resistant layer on at least one surface ofthe wood composite material.

According to other embodiments, the at least partially hydrogenatedpolymerized oils of the present disclosure may be used as a binder for afeed block and other agglomerated forms of animal feed. Feed blocks andother agglomerated forms of animal feed may be solidified mixtures ofagro-industrial by-products used for supplementing poor qualityroughages and native rangeland forages. They may be used as a catalystsupplement that may provide a fractionated, synchronized, and balancedsupply of nutrients (i.e., energy, nitrogen, minerals, vitamins, and thelike) for animals consuming diets that lack one or more of the nutrientsnecessary for a healthy diet. In addition, feed blocks and otheragglomerated forms of animal feed may also act as cost-effectivesupplements and as a means for preserving one or more high moistureagro-industrial by-products (for example, tomato pulp, olive cake, andthe like). Feed blocks and other agglomerated forms of animal feed mayprovide a useful alternative or complementary product to other feedproducts. Feed blocks and other agglomerated forms of animal feed areeasy to handle, transport, and can be made on site (i.e., at the animalproduction facility) as well as off site. A variety of formulae may beproduced incorporating different levels of urea, binders andagro-industrial by-products, depending on the animal's local needs andby-product availability. The at least partially hydrogenated polymerizedoils of the present disclosure may be incorporated into the feedformulations at 0.5 to 5% by weight of the total formula. In certainembodiments, feed blocks and other agglomerated forms of animal feedbenefit from the hydrophobicity of the at least partially hydrogenatedpolymerized oils of the present disclosure. The hydrophobicity of the atleast partially hydrogenated polymerized oils of the present disclosureconfers water-repellent characteristics to the feed blocks and otheragglomerated forms of animal feed, which confers improvements inweatherization of the feed blocks and other agglomerated forms of animalfeed. Therefore, according to certain embodiments, the feed blocks orother agglomerated forms of animal feed may be at least partiallymoisture resistant. Weatherization refers to the leaching of nutrientsfrom feed blocks and other agglomerated forms of animal feed on exposureto water, sunlight, and/or wind.

Nutrients and other components may be encapsulated in a moistureresistant feed block form using the at least partially hydrogenatedpolymerized oils of the present disclosure. Petroleum based products,such as, pariffinic and microcrystalline waxes, are used as binders tomake certain feed block formulations. In addition, use of the bindermaterials disclosed herein allows for the replacement of at least aportion of the petroleum products with the bio-based products. Whenconsumed by the animal, the polymerized oil containing binder materialmay be hydrolyzed by the digestive system of the animal to provideadditional energy. According to certain embodiments, the feed blocks andother agglomerated forms of animal feed may further comprise one or moreother ingredients, such as, for example, protein, non-protein nitrogensources (such as, but not limited to, urea), vitamins, minerals,palatability increasing agents, and agro-industrial by-products.Agro-industrial by-products include by-products produced during theproduction of agricultural products and/or industrial products andinclude, for example, tomato pulp, olive cake, date pulp, rice bran,vegetable meals, oilseed meals, animal proteins, grain co-products, suchas, brewery grains, distiller's grains, and corn germ meal, molasses,poultry waste, fermentation co-products, such as fermentation biomasses,yeast creams and yeast cakes, plant botanical extracts, such ascapsaicin, clove oil, cinnamaldehyde, and fenugreek, and variouscombinations thereof.

In other embodiments, the at least partially hydrogenated polymerizedoil may be used as a binder for an agricultural product, such as afertilizer, a pesticide, an herbicide, a fungicide, or a rodenticide.Certain agricultural products comprise components, including activeingredients and inert ingredients, which may be bound together with abinder, for example a binder comprising the at least partiallyhydrogenated polymerized oil, to form an aggregate particulate. The atleast partially hydrogenated polymerized oils of the present disclosuremay be incorporated into the aggregate formulations at 0.5% to 25% ofthe total formula by weight. In another embodiment, the at leastpartially hydrogenated polymerized oils may be incorporated into theaggregate formulations at from 5% to 10% of the total formulation byweight. Alternatively, other agricultural products may comprise acentral portion in which an active ingredient, such as, a fertilizer, apesticide, an herbicide, a fungicide, or a rodenticide, may be bound toat least a portion of the surface of the central portion. For example,according to one embodiment, the at least partially hydrogenatedpolymerized oil may at least partially bind the active ingredient to atleast a portion of a surface of the agricultural product. Combinationsof any of the active ingredients, for example, but not limited to, thecombination of a fertilizer and one of a pesticide, an herbicide, and afungicide, in the agricultural product are also contemplated. In certainembodiments, the agricultural product comprising the at least partiallyhydrogenated polymerized oil as a binder may be at least partiallymoisture resistant.

In certain embodiments where the material comprises a binder for arodenticide, the active ingredient comprising one or more compounds thatare toxic if consumed or inhaled by rodents or absorbed through therodents skin, including those substances that have an LD₅₀ of less than50 mg/kg body weight. Suitable active rodenticides include, but are notlimited to, thallium, sodium monofluoroacetate, strychnine, zincphosphide, yellow phosphorous, arsenic, and combinations of any thereof.The various active ingredients (bound together with the binder material)may be mixed with an edible ingredient, such as, for example, molassesor peanut butter, and distributed in an area infested with rodents.

In other embodiments wherein the material is a binder for anagricultural product, the at least partially hydrogenated polymerizedoil may provide for the controlled release of the agricultural product.For example, the binder comprising the at least partially hydrogenatedpolymerized oil may provide for the controlled release of a fertilizer,a pesticide, an herbicide, or a fungicide, by slow decomposition orremoval of the binder by certain environmental conditions, for example,by dissolution by rain water, oxidative decomposition by UV light,melting by sunlight or heat, or decomposition by microbes, to releasethe active ingredient(s) (i.e., the active fertilizer component(s),pesticide(s), herbicide(s), or fungicide(s)). As the binder decomposesor is removed, the active ingredient may be exposed or released.

In pesticide formulations, inert ingredients may be used as carriermaterials. These inert ingredients comprise up to 99.8% of the pesticideformulation and may include petroleum distillates. According to certainembodiments, these petroleum derived products may be at least partiallyreplaced with the bio-based products of the present disclosure. Forexample, the at least partially hydrogenated polymerized oil may beused, in place of, or in addition to, petroleum products, to bind oradhere the pesticides to surfaces and/or control the pesticides releaseover time. For example, when the more volatile components of thepesticide formulation evaporate, the active ingredient(s) remain in theresidue comprising the at least partially hydrogenated polymerized oil.Further, the at least partially hydrogenated polymerized oil may allowfor the slow release of the pesticide over time and prevent it frombeing easily wash away by rain or irrigation.

Other embodiments of the material comprising the at least partiallyhydrogenated polymerized oil as a binder include use of the material asan asphalt binder. Asphalt is a plastic material which melts and flowsat high temperatures and becomes hard and glassy at low temperatures.Asphalt may comprise a complex cementitious mixture of bitumens derivedfrom petroleum manufacturing. Polymers, such as styrene butadienepolymers, have been added to the asphalt mixture to adjust or manipulatecertain characteristics of the resulting hardened asphalt. Styrenebutadiene modified asphalts may demonstrate greater ability to withstandtemperature extremes. For example, styrene butadiene modified asphalt ismore viscous at high temperatures and therefore resistant to rutting orshoving, and more ductile at low temperatures and therefore lessbrittle, more resistant to fatigue cracking, and provide a more adhesivebinder. According to certain embodiments, the binder materials of thepresent disclosure comprising the at least partially hydrogenatedpolymerized oil may be used as a binder material in asphaltapplications.

According to certain embodiments, the at least partially hydrogenatedheat bodied/polymerized oils demonstrate a melting point profile thatmay be suitable for use in asphalt applications. For example, oneembodiment of the at least partially hydrogenated polymerized oil (OKOM-2½, a polymerized linseed oil) has a broad melting point from about 0°C. to 25° C., with two secondary melting points at about 30° C. andranging from 35° C. to 47° C. The at least partially hydrogenatedpolymerized oils of the present disclosure may be incorporated into theasphalt formulations at 0.5-25% of the total formula by weight. Thismelting point profile allows the binder to have melted domains andcrystalline domains, which could help with impact resistant over a rangeof temperatures. In addition, according to certain embodiments, thebinder comprising the partially hydrogenated polymerized oils couldundergo an oxidative cure to crosslink the polymerized oil chains, whichmay result in an asphalt with improved durability and/or elastomericpolymer formation. In still other embodiments, a blend of the at leastpartially hydrogenated polymerized oil and non-hydrogenated polymerizedoil could be used in asphalt binder applications. Non-hydrogenatedpolymerized oils have very low melting points (for example, according toone embodiment, from −30° C. to −3° C.) and the combination with atleast partially hydrogenated polymerized oils may give a mixture with adesired range of temperature performance. Further, replacing at least aportion of the petroleum derived components in asphalt mixtures withmaterials comprising bio-based polymerized oil binders results in anasphalt composition that has a reduced content of petroleum derivedcomponents.

In other embodiments, the material comprising the at least partiallyhydrogenated polymerized oil may be used as a binder for a personal careproduct. For example, many personal care products, such as, for example,lotions, creams, moisturizers, hair gels, cosmetics, makeup, deodorantsticks, lip balm, sun screen products, lubricants, and jellies, mayinclude petroleum derived products, such as a petrolatum product.According to various embodiments, the at least partially hydrogenatedpolymerized oils of the present disclosure may replace at least aportion of one or more petrolatum products as a binder in a personalcare product. The at least partially hydrogenated polymerized oil may beincorporated into cosmetic formulations at from 0.5% to 100% of thetotal formula by weight. Suitable at least partially hydrogenatedpolymerized oils include those polymerized oils derived from soybeanoil, linseed oil, castor oil, sunflower oil, safflower oil, canola oil,palm olein, or rapeseed oil.

Petrolatum and other petroleum products are believed to cause someproblems upon application to the skin. For example, petroleum jelly,such as VASELINE®, cannot readily be absorbed by healthy skin andtherefore creates a thin film on the surface of the skin uponapplication. This thin film can block pores and prevent normal functionof the skin. Because of the hydrocarbon nature of the petrolatumproduct, the skin is not equipped to break down these compounds. Unlikethe petrolatum-type products, personal care products comprising thematerials of the present disclosure may be more readily decomposed bythe skin. For example, the polymerized oils of the present disclosurecomprise ester bonds, which may be hydrolyzed by esterases and lipasesin the skin.

The polymerized oil products may require deodorization to remove certainimpurities, such as free fatty acids which may cause itching and skinsensitization. Deodorization may be effected using conditions known tothose having ordinary skill in the art, for example using conditionssimilar to those for deodorizing vegetable oils, such as soybean oil.The deodorization may be effected on the vegetable oil prior toconversion to a polymerized oil, after conversion to a polymerized oilbut prior to hydrogenation, or after polymerization and hydrogenation.

In other embodiments of the present disclosure, the materials comprisingat least one of a heat bodied oil and an at least partially hydrogenatedpolymerized oil may be a coating. For example, the coating materialcomprising the at least partially hydrogenated polymerized oil may beused, for example, as a packaging coating, an edible food coating, anagricultural product coating, and a concrete mold release coating.

The coating materials may further comprise vegetable oil esters and/orpetrochemical products. For example, according to certain embodiments,the coating materials of the present disclosure may comprise a blend ofthe at least partially hydrogenated polymerized oil and a vegetable oilester. Suitable vegetable oil esters that may be blended with the atleast partially polymerized oil include, but are not limited to, alkylesters of hydrogenated, partially hydrogenated, and non-hydrogenatedvegetable oils, such as, for example, methyl esters of hydrogenatedsoybean oil, methyl esters of hydrogenated HEAR oil, methyl esters ofpalm oil, and combinations of any thereof. In other embodiments, thecoating materials described herein may be blended with a petrochemicalproduct, such as, but not limited to, paraffin waxes, microcrystallinewaxes, mineral oil, petroleum greases, and combinations of any thereof.According to certain embodiments the coatings described herein may bemoisture resistant wax coatings.

In certain embodiments, the coating materials of the present disclosuremay be a coating for an agricultural product, such as, a fertilizercoating, a pesticide coating, an herbicide coating, a fungicide coating,a rodenticide coating, or a coating for combinations of any of theseagricultural products. For example, many fertilizers are water solubleand would dissolve and wash into the soil or be absorbed by the plantduring the first irrigation or rainfall. This may limit the amount offertilizer that could be applied during a given application and mayrequire costly reapplication of the fertilizer. Similar problems mayexist with pesticides, herbicides, fungicides, and rodenticides. Onesolution to this problem is to coat or encapsulate the water solubleactive ingredient, for example, the fertilizer, the pesticide, theherbicide, fungicide, and/or the rodenticide, in a water insolublecoating, an at least partially water insoluble coating and/or an atleast partially moisture resistant coating, such as, the at leastpartially hydrogenated polymerized oils of the present disclosure.According to these embodiments, the polymerized oil coating may providefor the release of the water soluble core material over an extendedperiod of time. For example, over time, the polymerized oil coating maydecompose or be removed upon prolonged exposure to the environment, suchas sunlight (e.g. UV radiation), rain, heat, and/or cold, or bymicrobial decomposition.

According to certain embodiments, the agricultural product may be in aparticulate form and the coating material comprising the polymerized oilmay have a solid content, a glass transition temperature, and a blockingtemperature sufficient to promote coating of the agricultural productwithout causing agglomeration of the particulates. Use of thepolymerized oils of the present disclosure as a coating may allow forthe reduction or elimination of alkyd resins, polyvinylidenechloro-based latex compositions, or other petroleum derivatives in thecoating materials. For example, hydrogenated or partially hydrogenatedpolymerized oils may be used directly in a coating with no furtheroxidative cross-linking cure since they provide a flexible, hydrophobic,higher molecular weight coating. If the coating comprises a partiallyhydrogenated polymerized oil (IV ˜50-100), the coating may be cured toform a thermoset polymer, as described herein. Curing of the partiallyhydrogenated polymerized oils may be cured using an initiator, such as afree radical polymerization initiator, for example, a ketone peroxide,such as, methyl ethyl ketone peroxide, benzoyl peroxide, and cumeneperoxide. In other embodiments a curing or polymerization promoter maybe including in the coating. Such a promoter may decrease the time ofcuring, for example, by speeding up the polymerization reaction.Examples of promoters include, but are not limited to, metals or metalcompounds, such as cobalt or vanadium and their compounds. In otherembodiments, the coating may be cured without addition of an initiator,such as, by a thermal or light (hν) mediated cure. Thus, the presentdisclosure may provide for coated or encapsulated agricultural productscomprising 100% bio-based material, in comparison to the petrochemicalderived materials seen in the prior art.

In other embodiments, the at least partially polymerized oils may beused as a coating for an food product or an animal feed. For example,according to one embodiment, the coatings comprising the at leastpartially polymerized oils of the present disclosure may be used as ananimal feed coating. That is, animal feed compositions and supplementsmay be coated with the coating compositions of the present disclosure toprevent degradation by environmental conditions and/or ready digestionby the upper digestive tract.

According to one embodiment wherein the coating is an animal feedcomposition coating configured to prevent degradation of the compositionby environmental conditions, the coating may be an at least partiallywater resistant coating, such that the coated feed composition is atleast partially resistant to degradation (e.g., loss of nutrients,structural integrity, and/or palatability) by exposure to rain and/orwind. In other embodiments, the coating may provide the coated materialsresistance to degradation by microbes, mold, insects, and the like. Inaddition, use of the coating of the present disclosure may improvephysical handling characteristics and shelf-life stability of the coatedanimal feed compositions and supplements. In specific examples ofagglomerated, loose mineral applications, the at least partiallypolymerized oils of the present disclosure may be used to agglomeratethe micronutrients (for example, but not limited to, zinc, manganese,copper, cobalt, vitamins, and the like) to achieve a more uniformparticle size for the finished mineral product when combined withmacro-ingredients (e.g., monocalcium phosphate, limestone, defluorinatedphosphate, and other macro-ingredients know in the art). Coatingscomprising the at least partially polymerized oils may comprise from0.1% to 5% by weight of the total feed formula.

According to other embodiments, the coatings comprising the at leastpartially hydrogenated polymerized oils of the present disclosure mayprovide for increase rumen bypass of proteins, fats, and non-proteinnitrogen (such as, urea) in animal feed compositions by reducing therumen fermentation of the animal feed compositions. For example, incertain cases it may be desirable to increase the amount of protein in aruminant's diet that passes substantially intact through the rumen andinto the latter portions of the ruminant digestive tract (i.e., smallintestine). Thus, the coating comprising the at least partiallyhydrogenated polymerized oil may prevent digestion of at least a portionof the animal feed composition in the rumen by preventing the rumenmicrobes from metabolizing at least a portion of the proteins, fats, andnon-protein nitrogen in the animal feed. In certain embodiments, thecoating may be a coating on an animal feed such as an animal feedcomprising an ingredient selected from the group consisting of animalproteins, animal fats, plant proteins, plant oils, non-protein nitrogensources, and combinations of any thereof, wherein an amount of theanimal feed passing at least partially intact through a rumen of aruminant is increased compared to an animal feed that is not coated withthe animal feed coating. In certain embodiments, the animal feedcoatings may comprise between 0.01% to 10% by weight of the total animalfeed.

In another embodiment, the coatings materials comprising the at leastpartially hydrogenated polymerized oils of the present disclosure may bean edible food coating, such as a fruit coating or a vegetable coating.

For example, in one embodiment, the coating material may be an ediblefruit coating or a vegetable coating. Edible lipid coatings for fruitsand vegetables may provide a barrier for prevention of moisture loss aswell as giving the fruit or vegetable a desirable glossy surface andcolor. However, in order for the coating to be effective, the lipid mustadhere to the fruit/vegetable surface, form a continuous barrier, andremain intact over a wide temperature range. Attempts to use liquidfats, such as vegetable oils, for edible coatings can result in thecoating material's failure to adhere to the fruit/vegetable surface,particularly at warmer temperatures. Attempts to use other lipids suchas solid fats and paraffin wax resulted in a coating that may be toobrittle when cool or too thick to apply directly (depending on thenature of the fat). According to certain embodiments, the at leastpartially hydrogenated polymerized oils of the present disclosure may beused in edible coatings for fruits and vegetables. The polymerized oilsmay provide a coating that is easily applicable, adheres well to thefood surface, forms a continuous barrier (such as a moisture barrier),and remain intact, yet pliable over a wide temperature range. In certainembodiments, the coating material may comprise the at least partiallyhydrogenated polymerized oil. In other embodiments, the coating materialmay further comprise at least one emulsifier, such as, but not limitedto, monoacylglycerols and diacylglycerols, gums, such as xanthan gum,propylene glycol alginate, carboxy methyl cellulose, gum Arabic, locustbean gum, maltodextrin, fatty alcohol ethoxylates, fatty acidethoxylates, sorbitan derivatives, polyglycerol esters, lecithin, andcombinations of any thereof. According to certain embodiments, thecoating material may comprise from 0.01% to 50% by weight of the atleast partially hydrogenated polymerized oil. The coating material maybe applied to the fruit or vegetable as an emulsion, such as a lipidhydrocolloid emulsion, that forms a continuous or partial barrier. Theresulting edible coating will maintain flexibility (i.e., not flake off)over a wide temperature range.

In other embodiments, the coatings comprising the at least partiallyhydrogenated polymerized oil of the present disclosure may be apackaging coating. In one embodiment, the material may be a packagingcoating for a corrugated cardboard material. In another embodiment, thecoating material may be a flexible packaging coating. While hydrogenatedvegetable oil has been used as a packaging coating for corrugatedcardboard, the hydrogenated vegetable oil does not readily penetrate thecardboard surface and had a tendency to crack and flake when thecardboard was bent. In contrast, the packaging coating material of thepresent disclosure demonstrates good surface penetration and does notreadily crack or flake. The resulting coating also shows excellentmoisture resistance.

According to various embodiments wherein the coating material is apackaging coating, the coating material may be applied to at least aportion of a surface of the packaging material, for example by sprayingthe coating material onto the portion of the packaging surface, or bydipping the packaging material into the coating material, such as afterthe coating material has been heated into liquid form. Excess liquidcoating material may be removed, such as, by shaking, agitating, orwiping such that the coating material forms a smooth coating having asubstantially uniform thickness over the coated portion of the packagingsurface. Upon cooling, the coating material may solidify into a waxcoating that maintains flexibility and moisture resistance. In certainembodiments, the coating material may further comprise esters, such asmethyl esters (for example partially hydrogenated soybean methyl esters,methyl esters of hydrogenated soybean oil, methyl esters of hydrogenatedHEAR oil, methyl esters of palm oil, methyl esters of fractionated oils,and combinations of any thereof) and propylene glycol monoesters (forexample propylene glycol monostearate). For example, lower molecularweight methyl esters may improve surface penetration of the coating,aiding overall adhesion and reducing flaking and cracking. Packagingcoating of the present disclosure comprising additional esters, maycomprise from 0.01% to 30% by weight of the at least partiallyhydrogenated polymerized oil and 30% to 70% by weight of the additionalesters.

In other embodiments, the packaging coating material for cardboard, suchas corrugated cardboard, may comprising the at least partiallyhydrogenated polymerized oil and a petroleum derived wax. The at leastpartially hydrogenated polymerized oil may be blended with the petroleumderived wax and then the cardboard may be coated with the blend.According to certain embodiments, the packaging coating material maycomprise from 0.01% to 10% by weight of the at least partiallyhydrogenated polymerized oil. The coated cardboard may then be resistantto moisture and also resistant to cracking and/flaking when thecardboard is bent.

In still other embodiments, the coating materials of the presentdisclosure may comprise a concrete or cement release coating. During thepouring and curing of concrete/cement, the concrete/cement may adhere tothe surface of the mold or form during hardening, resulting in afinished product in which the surfaces are pitted and uneven. Coating atleast a portion of the mold or form surface with a release coating mayprevent adhesion of the concrete/cement. The at least partiallyhydrogenated polymerized oils of the present disclosure may be used as aconcrete/cement release coating.

In certain embodiments, where the coating comprising the at leastpartially hydrogenated polymerized oil is a concrete mold releasecoating, the coating material may further comprise at least oneadditional component, such as, for example, a vegetable oil, an alcohol(for example, ethanol, propanol, butanol, and mixture thereof), a fuseloil mixture, a lactate ester (such as ethyl lactate), a fatty acidmethyl ester, a propylene glycol monoester, and combinations of anythereof. For example, according to certain embodiments, the concretemold release coating may comprise from 0.01% to 10% by weight of the atleast partially hydrogenated polymerized oil.

Other embodiments of the present disclosure provide for a candle wax orcandle comprising an at least partially hydrogenated polymerized oil.The candles according to these embodiments may be a gel candle or candlewax (i.e., a container candle) or a hard candle or candle wax, dependingon the degree of hydrogenation of the polymerized oil (that is, thegreater degree of hydrogenation, the harder the candle material. Incertain embodiments, the candle wax or candle may optionally comprise atleast one additional additive, such as a vegetable oil, an alkyl ester(such as a propylene glycol monoester), a perfume, a scent, a petroleumderivative (such as a paraffin wax or other petroleum-based wax) andcombinations of any thereof. These additional additives may modify thewaxy structure of the candle, for example, to provide a smoothappearance without noticeable crystallinity, a desirable morphologyand/or texture. The resulting candles are shelf stable, showing nocracking or discoloration after storage for one year at roomtemperature.

According to other embodiments, the present disclosure provides apolymer composition comprising the heat bodied oils or partiallyhydrogenated polymerized oil, wherein at least one of the remainingcarbon-carbon double bonds in the heat bodied/partially hydrogenatedpolymerized oil has been converted to at least one epoxide. The IV valueof the partially hydrogenated polymerized oil may range from essentiallyzero (i.e. greater than zero) up to the IV of the initial polymerizedoil. In certain embodiments, the IV value for the partially hydrogenatedoil may range from 50 to 120. The at least one of the remainingcarbon-carbon double in the partially hydrogenated polymerized oil maybe converted to the at least one epoxide by either a chemical orenzymatic epoxidation method. For example, suitable chemical epoxidationmethods include hydrogen peroxide epoxidation, peroxy acid epoxidations,oxone epoxidations, and other epoxidation methods known in the art.Enzymatic epoxidations may involve epoxidase enzymes. In certainembodiments all of the remaining carbon-carbon double bonds areepoxidized.

The polymer composition wherein at least one of the remainingcarbon-carbon double bonds of the partially hydrogenated polymerized oilhas been converted to a least one epoxide may be used in a variety ofchemical reactions to produce new polymer compositions. Theepoxy-bearing polymerized oils may react with nucleophiles (vianucleophilic attack, for example by amines, alcohols, water, and othernucleophiles) to produce a ring opened alcohol product. For example,acid or base catalyzed ring opening may produce alcohols (hydride asnucleophile), vicinal diols (water as nucleophile), 1,2-hydroxy ethers(alcohol as nucleophile), 1,2-amino alcohols (amine as nucleophile),1,2-hydroxy esters (carboxylate as nucleophile), and the like. Theresulting hydroxyl polymerized oils may be used as a component in apolyurethane polymerization. For example, polymerized oils having, onaverage, two or more hydroxyl groups per molecule may be reacted with adiisocyanate to produce a polyurethane. The resulting polyurethane maybe suitable for use in fibers, hard and soft elastomers, coatings andadhesives, flexible and rigid foams, and thermoplastics andthermosetting plastics. Thus, certain embodiments of the presentdisclosure contemplate a polyurethane comprising at least one of a heatbodied oil or an at least partially hydrogenated polymerized oil.

Alternatively, the epoxy containing polymerized oil may be used as anHCl scavenger. In other embodiments, the epoxy containing polymerizedoil may be used as a plasticizer, a lubricant, and/or an additive in PVCor other plastic compounding applications. In certain embodiments, theepoxidized polymerized oils may be added into epoxy coating/compositesas part of an epoxy resin system.

In other embodiments, the present disclosure provides for a greasecomprising an at least partially hydrogenated polymerized oil and atleast one metal salt of a free fatty acid. For example, polymerized oilsthat have been kettle-bodied without vacuum may have a higher free-fattyacid content than those produced under vacuum. Such polymerized oils maybe used as a heavy grease for lubrication applications. The free fattyacids in the polymerized oil may be converted to the metal salt, such asthe lithium salt, to produce a stabilized grease type composition.However, unlike most typical greases which are derived from petroleumsources, the grease comprising the polymerized oil will be 100%bio-based. According to various embodiments, the grease may comprisefrom 0.01% to 100% by weight of the at least partially hydrogenatedpolymerized oil.

Various embodiments of the present disclosure will be better understoodwhen read in conjunction with the following non-limiting Examples. Theprocedures set forth in the Examples below are not intended to belimiting herein, as those skilled in the art will appreciate thatvarious modifications to the procedures set forth in the Examples, aswell as to other procedures not described in the Examples, may be usefulin practicing the invention as described herein and set forth in theappended claims.

Examples Example 1 Hydrogenation of P—S Gardener Viscosity Heat BodiedLinseed Oil

Alinco Q (commercially available from Archer Daniels-Midland, Decatur,Ill., (hereinafter “ADM”)) was used as the starting material. The rawmaterial specifications of Alinco Q include a Gardener viscosity of P—Sand an iodine value of 130-150. Alinco Q (600 g) was added to a 1 Lstainless steel reaction vessel with 3 g of a nickel catalyst (G-53, SudChemie, Louisville, Ky.). The vessel was purged with hydrogen five timesand then pressurized to 200 psig. The reaction was the heated to 230° C.After reaching 230° C., the reaction vessel was pressurized to 300 psig.A continuous feed of hydrogen gas was used holding the pressure of thevessel at 300 psig for 16 h.

Example 2 Hydrogenation of X Gardener Viscosity Heat Bodied Linseed Oil

Alinco X (ADM) was used as the starting material. The raw materialspecifications of Alinco X include a Gardener viscosity of X and aniodine value of 120-130. Alinco X (600 g) was added to a 1 L stainlesssteel reaction vessel with 3 g of a nickel catalyst (G-53, Sud Chemie,Louisville, Ky.). The vessel was purged with hydrogen five times andthen pressurized to 200 psig. The reaction was the heated to 230° C.After reaching 230° C., the reaction vessel was pressurized to 300 psig.A continuous feed of hydrogen gas was used holding the pressure of thevessel at 300 psig for 16 h. The reaction was then cooled and filteredto remove the nickel catalyst. The IV of the final product was 10.5.

Example 3 Hydrogenation of X Gardener Viscosity Heat Bodied Soybean Oil

Heat bodied soybean oil with an X Gardener viscosity (ADM) was used asthe starting material. X-bodied soy (600 g) was added to a 1 L stainlesssteel reaction vessel with 6 g of a nickel catalyst (G-53, Sud Chemie,Louisville, Ky.). The vessel was purged with hydrogen five times andthen pressurized to 200 psig. The reaction was the heated to 230° C.After reaching 230° C., the reaction vessel was pressurized to 300 psig.A continuous feed of hydrogen gas was used holding the pressure of thevessel at 300 psig for 16 h. The reaction was then cooled and filteredto remove the nickel catalyst.

Example 4 Hydrogenation of Y Gardener Viscosity Heat Bodied Linseed Oil

Alinco Y (ADM) was used as the starting material. The raw materialspecifications of Alinco Y include a Gardener viscosity of Y and aniodine value of 120-130. Alinco Y (600 g) was added to a 1 L stainlesssteel reaction vessel with 6 g of a nickel catalyst (G-53, Sud Chemie,Louisville, Ky.). The vessel was purged with hydrogen five times andthen pressurized to 200 psig. The reaction was the heated to 230° C.After reaching 230° C., the reaction vessel was pressurized to 300 psig.A continuous feed of hydrogen gas was used holding the pressure of thevessel at 300 psig for 16 h. The reaction was then cooled and filteredto remove the nickel catalyst.

Example 5 Hydrogenation of Z₄ Gardener Viscosity Heat Bodied Linseed Oil

OKO M 2½ (ADM) was used as the starting material. The raw materialspecifications of OKO M 2½ include a Gardener viscosity of Z₄ and aniodine value of 115-130. OKO M 2½ (600 g) was added to a 1 L stainlesssteel reaction vessel with 6 g of a nickel catalyst (G-53, Sud Chemie,Louisville, Ky.). The vessel was purged with hydrogen five times andthen pressurized to 200 psig. The reaction was the heated to 230° C.After reaching 230° C., the reaction vessel was pressurized to 300 psig.A continuous feed of hydrogen gas was used holding the pressure of thevessel at 300 psig for 16 h. The reaction was then cooled and filteredto remove the nickel catalyst. The IV of the final product was 15.5.

Example 6 Hydrogenation of Z₉ Gardener Viscosity Heat Bodied Linseed Oil

OKO M-37 (ADM) was used as the starting material. The raw materialspecifications of OKO M-37 include a Gardener viscosity of Z₉ and aniodine value of 115-130. OKO M-37 (600 g) was added to a 1 L stainlesssteel reaction vessel with 6 g of a nickel catalyst (G-53, Sud Chemie,Louisville, Ky.). The vessel was purged with hydrogen five times andthen pressurized to 200 psig. The reaction was the heated to 230° C.After reaching 230° C., the reaction vessel was pressurized to 300 psig.A continuous feed of hydrogen gas was used holding the pressure of thevessel at 300 psig for 16 h. The reaction was then cooled and filteredto remove the nickel catalyst.

TABLE 1 Hydrogenated Bodied Oil Test Data Kinematic Congealing ConePenetration Viscosity (ASTM Point (ASTM (ASTM D937) Sample D445) (cSt)D938) (° F.) (dmm) Example 1 33.0 84 too soft Example 4 73.0 97 126Example 5 157 95  95 Example 6 N/A* 93 222 *Data out of viscosity range.

Example 7 Polyglycerol Esters of Behenic Acid as Crystal Enhancer

Triglycerol (Solvay, Houston, Tex.) and methyl behenate (Proctor &Gamble, Cincinnati, Ohio) and potassium carbonate were added to a 250 mLroundbottom flask equipped with mechanical stirring, a barret stylereceiver, condenser and nitrogen purge. The reaction was carried out at165° C. for six hours with removal of methanol. The resulting materialwas a hard solid waxy material with a melting point about 80° C. Thismaterial could be added to hydro-bodied oils, described in previousexamples, to modify the crystallinity, physical properties, and meltingpoint of the final material.

Example 8 Hydro Soy/HEAR Oil as Crystal Enhancer for Hydro Bodied-Oils

A blend of fully hydrogenated soy oil and HEAR oil (50 g) was added tohydro-bodied oil (OKO M-2½) in Example 5 (50 g). The components werefully miscible and were blended in the liquid state. The resultingmaterial had a higher melting point and increased hardness in comparisonto the hydro-bodied oil in example 4. Hydrogenated soy/HEAR oil could beadded to hydro-bodied oils, described in previous examples, to modifythe crystallinity, physical properties, and melting point of the finalmaterial.

Congeal Point (ASTM D938) 120° F. Drop Melt Point (ASTM D127) 138° F.Kinematic Viscosity @ 210° F. (ASTM D445) 37 cst. Needle Penetration @77° F. (ASTM D1321) 25 dmm

Example 9 Partial Hydrogenation of Z₄ Gardener Viscosity Heat BodiedLinseed Oil

OKO M 2½ (ADM) was used as the starting material. The raw materialspecifications of OKO M 2½ include a Gardener viscosity of Z₄ and aniodine value of 115-130. OKO M 2½ (600 g) was added to a 1 L stainlesssteel reaction vessel with 3 g of a nickel catalyst (G-53, Sud Chemie,Louisville, Ky.). The vessel was purged with hydrogen five times andthen pressurized to 200 psig. The reaction was the heated to 230° C.After reaching 230° C., the reaction vessel was pressurized to 300 psig.A continuous feed of hydrogen gas was used holding the pressure of thevessel at 300 psig. Samples were taken every hour for four hours. Thereaction was then cooled and filtered to remove the nickel catalyst. TheIV of the final product (4 hour) was 57.8. See Table 2 for IV results.

Example 10 Partial Hydrogenation of X Gardener Viscosity Heat BodiedLinseed Oil

Alinco X (ADM) was used as the starting material. The raw materialspecifications of Alinco X include a Gardener viscosity of X and aniodine value of 120-130. Alinco X (600 g) was added to a 1 L stainlesssteel reaction vessel with 3 g of a nickel catalyst (G-53, Sud Chemie,Louisville, Ky.). The vessel was purged with hydrogen five times andthen pressurized to 200 psig. The reaction was the heated to 230° C.After reaching 230° C., the reaction vessel was pressurized to 300 psig.A continuous feed of hydrogen gas was used holding the pressure of thevessel at 300 psig. Samples were taken every hour for four hours. Thereaction was then cooled and filtered to remove the nickel catalyst. TheIV of the final product (4 hour) was 40.2. See Table 2 for IV results.

TABLE 2 Iodine Values of Bodied Oils at Various Reaction Times Sample 1h 2 h 3 h 4 h OKO M2 ½ 95.8 79.1 64.5 57.8 (example 9) Alinco X 69.247.8 40.9 40.2 (example 10)

Example 11 Hydro Soy Oil as Crystal Enhancer for Hydro Bodied-Oils

A blend of 2 IV fully hydrogenated soy oil (50 g) was added tohydro-bodied oil (OKO M 2½) in example 5 (50 g). The components werefully miscible and were blended in the liquid state. The resultingmaterial had a higher melting point and increased hardness in comparisonto the hydro-bodied oil from example 5. Hydrogenated soy oil could beadded to hydro-bodied oils, described in previous examples, to modifythe crystallinity, physical properties, and melting point of the finalmaterial.

Congeal Point (ASTM D938) 124° F. Drop Melt Point (ASTM D127) 126° F.Kinematic Viscosity @ 210° F. (ASTM D445) 38.5 cst. Needle Penetration @77° F. (ASTM D1321) 41 dmm

Example 12 Hydro Soy Oil and Behenic Acid Esters of Triglycerol asCrystal Enhancer for Hydro Bodied-Oils

A blend of 2 IV fully hydrogenated soy oil (36 g) and Behenic acidesters of triglycerol (4 g) was added to hydro-bodied oil (OKO M 2½)from example 5 (40 g). The components were fully miscible and wereblended in the liquid state. The resulting material had a higher meltingpoint and increased hardness in comparison to the hydro-bodied oil inexample 4. Hydrogenated soy oil could be added to hydro-bodied oils,described in previous examples, to modify the crystallinity, physicalproperties, and melting point of the final material.

Congeal Point (ASTM D938) 130° F. Drop Melt Point (ASTM D127) 133° F.Kinematic Viscosity @ 210° F. (ASTM D445) 40.7 cst. Needle Penetration @77° F. (ASTM D1321) 45 dmm

Example 13 Deodorization of Hydro Bodied Oils

Residual free fatty acids are present in heat bodied oils. These freefatty acids along with residual odor-causing byproducts of hydrogenationcan be removed from the hydro bodied oils by deodorization.Deodorization is a process used in the refining of vegetable oils (Y. H.Hui, ed. Bailey's Industrial Oil and Fat Products, 5th edition, Vol. 2,p 537-540, incorporated in its entirety by reference herein). Hydro OKOM 2½ was deodorized at 230° C. for 30 min under a vacuum of about 1torr. The steam rate for the run was approximately 5% water on the oil.

Example 14

Hydrogenated bodied linseed oil (hydrogenated OKO M 2½, ADM), NuSunsunflower oil (ADM) and a 50/50 mixture of hydro soy/hydro high erucicacid rapeseed (HEAR) oil were blended at the following amounts:

50 g NuSun Oil

25 g Hydrogenated OKO M 2½

25 g 50/50 hydro soy/hydro HEAR

The above materials were mixed in the liquid state above 60° C. When themixture reached 60° C., it was then placed in a refrigerator at 5° C. tofinish cooling. The final material was an opaque material that had aconsistency similar to petroleum jelly.

Example 15

Hydrogenated bodied soybean oil (hydrogenated X-bodied soybean oil,ADM), RBD Soybean oil (ADM) and behenic acid esters of triglycerol wereblended at the following amounts:

50 g RBD Soybean Oil

49 g Hydrogenated Bodied Soybean Oil (X-Bodied Soybean Oil)

1 g Behenic acid esters of triglycerol

The above materials were mixed in the liquid state above 60° C. When themixture reached 60° C., it was then placed in a refrigerator at 5° C. tofinish cooling. The final material was an off-white, opaque semi-solidthat had a consistency similar to petroleum jelly.

Example 16

Hydrogenated bodied linseed oil (hydrogenated OKO M 2½, ADM), NuSunsunflower oil (ADM) and partially hydrogenated soybean oil were blendedat the following amounts:

50 g NuSun Oil

25 g Hydrogenated OKO M 2½

25 g Partially hydrogenated soybean oil (42 IV)

The above materials were mixed in the liquid state above 60° C. When themixture reached 60° C., it was then placed in a refrigerator at 5° C. tofinish cooling. The final material was an off-white, opaque, viscousliquid that had a consistency similar to petroleum jelly.

Example 17

Hydrogenated bodied linseed oil (hydrogenated OKO M 2½, ADM),hydrogenated bodied soybean oil (hydrogenated X-bodied soybean oil,ADM), NuSun sunflower oil (ADM), a 50/50 mixture of hydro soy/hydro higherucic acid rapeseed (HEAR) oil and Vitamin E (ADM) were blended at thefollowing amounts:

40 g Hydrogenated OKO M 2½

25 g NuSun Oil

24 g Hydrogenated X-Bodied Soybean Oil

10 g 50/50 hydro soy/hydro HEAR

1 g Vitamin E, 100% d-alpha tocopherol

The above materials were mixed in the liquid state above 60° C. When themixture reached 60° C., it was then placed in a refrigerator at 5° C. tofinish cooling. The final material was an off-white, opaque semi-solidthat had a consistency similar to petroleum jelly.

Example 18 Hydrogenation of a Heavy Bodied Blown Linseed Oil

Heavy bodied blown linseed oil (ADM) was used as the starting material.The blown linseed oil (600 g) was added to a 1 L stainless steelreaction vessel with 6 g of a nickel catalyst (G-53, Sud Chemie,Louisville, Ky.). The vessel was purged with hydrogen five times andthen pressurized to 200 psig. The reaction was then heated to 230° C.After reaching 230° C., the reaction vessel was pressurized to 300 psig.A continuous feed of hydrogen gas was used holding the pressure of thevessel at 300 psig for 6 h. The reaction was then cooled and filtered toremove the nickel catalyst. The final material was an opaque yellowsolid with a hydroxyl value of 77.5, and an IV value of 18.1.

Example 19 Hydrogenation of Blown Soybean Oil

Blown soybean oil (Cargill 680 Blown Soybean Oil, Cargill, Minneapolis,Minn.) was used as the starting material. The blown soybean oil (600 g)was added to a 1 L stainless steel reaction vessel with 6 g of a nickelcatalyst (G-53, Sud Chemie, Louisville, Ky.). The vessel was purged withhydrogen five times and then pressurized to 200 psig. The reaction wasthen heated to 230° C. After reaching 230° C., the reaction vessel waspressurized to 300 psig. A continuous feed of hydrogen gas was usedholding the pressure of the vessel at 300 psig for 6 h. The reaction wasthen cooled and filtered to remove the nickel catalyst. The finalmaterial was an opaque yellow solid with a hydroxyl value of 93.

Example 20 Hydrogenation of ML-189 (Dicyclopentadiene-Linseed OilCopolymer)

ML-189 (600 g), manufactured by ADM, was added to a 1 L stainless steelreaction vessel with 3 g of a nickel catalyst (G-53, Sud Chemie,Louisville, Ky.). The vessel was purged with hydrogen five times andthen pressurized to 200 psig. The reaction was the heated to 230° C.After reaching 230° C., the reaction vessel was pressurized to 300 psig.A continuous feed of hydrogen gas was used holding the pressure of thevessel at 300 psig for 8 h. After hydrogenation, the signal at about 5.2ppm corresponding to the olefin component was not present in the ¹H NMRspectrum. The hydrogenated material was a hard wax-like solid at roomtemperature with a melting point of 44.7° C. (Mettler drop point).

Example 21 Hydrogenation of Toplin X-Z (Linseed Oil Copolymer)

Toplin X-Z (600 g), manufactured by ADM, was added to a 1 L stainlesssteel reaction vessel with 3 g of a nickel catalyst (G-53, Sud Chemie,Louisville, Ky.). The vessel was purged with hydrogen five times andthen pressurized to 200 psig. The reaction was the heated to 230° C.After reaching 230° C., the reaction vessel was pressurized to 300 psig.A continuous feed of hydrogen gas was used holding the pressure of thevessel at 300 psig for 8 h. The hydrogenated material was a hardwax-like solid at room temperature with a melting point of 49.9° C.(Mettler drop point). After hydrogenation, the signal at 5.2 ppmcorresponding to the olefin component was not present in the ^(I)H NMRspectrum.

Example 22 Partial Hydrogenation of Toplin X-Z (Linseed Oil Copolymer)

Toplin X-Z (600 g), manufactured by ADM, was added to a 1 L stainlesssteel reaction vessel with 3 g of a nickel catalyst (G-53, Sud Chemie,Louisville, Ky.). The vessel was purged with hydrogen five times andthen pressurized to 200 psig. The reaction was the heated to 230° C.After reaching 230° C., the reaction vessel was pressurized to 300 psig.A continuous feed of hydrogen gas was used holding the pressure of thevessel at 300 psig for 2 h. The hydrogenated material was a softsemi-solid material. After hydrogenation, ¹H NMR analysis indicated thatthe signal at 5.2 ppm corresponding to the olefin component was reducedby 50%.

Example 23 Blend of Hydrogenated Heat Bodied Oil and Hydrogenated HEAROil

Hydrogenated bodied linseed oil (OKO M 2½, ADM), 100 g, was melted andmixed with 100 g of melted hydrogenated HEAR (high erucic acid rapeseed)oil. The mixture was then allowed to cool to room temperature. At roomtemperature, the mixture was a white, hard, waxy solid. Peak meltingpoint was about 58° C.

Example 24 Blend of Hydrogenated Heat Bodied Oil and Hydrogenated CastorOil

Hydrogenated bodied linseed oil (OKO M 2½, ADM), 100 g, was melted andmixed with 100 g of melted hydrogenated castor oil (Sud Chemie,Louisville, Ky.). The mixture was then allowed to cool to roomtemperature. At room temperature, the mixture was a white, hard, waxysolid. Mettler drop point was 85.8° C. Peak melting point was about 80°C.

Example 25 Interesterification of Hydro-Heat Bodied Oils withTriacylglycerols

Heat bodied linseed oil (OKO M 2½, ADM) having a Gardener viscosity ofZ4 and an IV of 115-130 was hydrogenated as follows. The heat bodiedlinseed oil (OKO M 2½, 600 g) was added to a 1 L stainless steelreaction vessel with 6 g of a nickel catalyst (G-53, Sud Chemie,Louisville, Ky.). The vessel was purged with hydrogen five times andthen pressurized to 200 psig of hydrogen. The reaction was heated to230° C. After reaching 230° C., the reaction vessel was pressurized to300 psig. A continuous feed of hydrogen gas was used, holding thepressure of the vessel at 300 psig for 16 h. The reaction was thencooled and filtered to remove the nickel catalyst. The IV of the productwas 15.5.

The hydrogenated heat bodied linseed oil was chemically interesterifiedwith an equal weight of fully hydrogenated soybean oil. Hydrogenated OKO2½ (50 grams) was combined with fully hydrogenated soybean oil (DritexS) in a 500 ml round bottom flask. Vacuum (20 psi) was applied and themixture was heated to 90° C. for one hour to remove any traces of water.Interesterification catalyst (sodium methoxide; 0.3 grams; 5.56millimoles) was added and the mixture was heated to 140° C. for 2 hoursto carry out interesterification. The interesterified product wasallowed to cool below 100° C. and was mixed with a solution of citricacid containing 5.56 millimoles of citric acid. The mixture of washsolution and interesterified product was transferred to a hot separatoryfunnel. The wash layer was removed, and the interesterified product waswashed with four water washes, after which the pH value of the used washsolution was neutral. The resulting material retained a desirable highmelting point, with a transition temperature of 53.1° C., but wassignificantly less brittle than fully hydrogenated soybean oil. FIG. 1illustrates the differential scanning calorimetry (DSC) scans of thestarting materials (Dritex, the fully hydrogenated soybean oil and theheat bodied linseed oil) and the interesterified product (wax-OKO).

Example 26 Hot Melt Adhesive Formulations

For the purpose of demonstrating the utility of the polymerized oil inhot melt adhesive applications, evaluations are conducted to determinethe performance of hydrogenated and partially hydrogenated polymerizedvegetable oils versus a control petroleum derived microcrystalline waxin standard hot melt ethylene vinyl acetate (“EVA”) formulations. Oneseries of tests includes high vinyl acetate (28%) content, whereas theother series includes low vinyl acetate (18%) content. The ingredientsare added on a weight basis. The compositions of the formulations are inTable 3. The hot melt adhesive compositions are made according to thedisclosure of U.S. Application Publication No. US20030229168A1, thedisclosure of which is incorporated in its entirety by reference herein.

TABLE 3 Composition of Hot-Melt Adhesive Formulations (all units ingrams) Control Material 1 Material 2 High VA Content Formulations (28%VA in resin) EVA (28% VA) 200 200 200 Tackifier (FORAL 85) 200 200 200Wax-control 200 200 Material 1 200 Material 2 200 Thermal stabilizer(IRGANOX 1010) 6 6 6 Low VA Content Formulations (18% VA in resin) EVA(18% VA) 200 200 200 Tackifier (FORAL 85) 200 200 200 Wax-control 200Material 1 200 Material 2 200 Thermal stabilizer (IRGANOX 1010) 6 6 6

The formulations include ULTRATHENE® 612-04 (EVA resin with 18% vinylacetate content, commercially available from Equistar Chemicals, LP,Houston Tex.), ULTRATHENE® 646-04 (EVA resin with 28% vinyl acetatecontent, commercially available from Equistar Chemicals, LP, HoustonTex.), FORAL® 85 resin ester tackifier (commercially available fromHercules, Wilmington, Delaware), IRGANOX® 1010 thermal stabilizer(commercially available from Ciba-Geigy, Tarrytown, N.Y.). The controlformulation includes microcrystalline wax (commercially available fromFrank B. Ross Co., Rahway, N.J.), whereas Material 1 compriseshydrogenated polymerized soybean oil and Material 2 comprises partiallyhydrogenated polymerized soybean oil. The compositions are blended in aquart can heated by a glass heating mantle, as follows. Tackifier andstabilizer are added into the can and the mixture allowed to heat for 10minutes to ensure uniformly melted material. Mixing is started at amoderate rate of speed while the EVA is slowly added over 25 minutes.While mixing is continued, the wax/polymerized oil is slowly added intothe adhesive over a 15 minute period. The resulting adhesive mixture isallowed to mix for an additional 15 minutes to assure uniformity. Thefinal adhesive temperature ranges from 350° F. to 360° F.

Example 27 Moisture Resistant Cardboard Coating

In this Example, corrugated cardboard strips were coated and tested formoisture resistance and flexibility.

Hydrogenated heat bodied linseed oil (OKO M 2½, 50 g, ADM) having an IVof 31.6 was mixed with propylene glycol monostearate blend additive (50g, 90% monoester, Aldo-90 Lonza, Allendale, N.J.). The mixture wasmelted and mixed together. Corrugated cardboard squares were cut from abox and dipped into the melted mixture for 15-20 seconds. The meltedmaterial quickly penetrated the cardboard during the dipping procedure.After dipping, the excess material was removed. The treated cardboardstrips were resistant to water penetration and did not crack (coatingcrack) when bent at a 45-90° angle (no flaking off of the coating wasobserved).

Cardboard coatings were prepared by melting basestock petroleum waxesand bioderived basestocks and optionally supplementing with a blendadditive (added at 2 wt % of the entire formulation. In a comparisontest, hydrogenated heat-bodied linseed oil was mixed with petroleumbased waxes (3 wt % hydrogenated OKO 2½ with 97 wt % petroleum wax) andtested for wax pick-up (penetration) and water pick-up (absorption). Thepetroleum waxes used in the blends were Citgo PM (commercially availablefrom Citgo Wax Laboratory, Sulphur, La.); Robwax 2309 (commerciallyavailable from C.J. Robison Company, Inc., Bridgeport, Pa.); Parvan 1270(commercially available from ExxonMobile, Baton Rouge, La.); and CalumetSC5717 (commercially available from Calumet Lubricants Co., Shreveport,La.). Dry 2 inch square corrugated cardboard squares were weighed tofour decimal places. Coating formula waxes were heated to 96-99° C. andeach square was coated by dipping the cardboard into the coating for15-20 seconds or pouring the coating over the cardboard. The coatedsamples were allowed to cool overnight and weighed again to determinethe wax pick-up (tests were done in triplicate). Coated samples weresubmerged in room temperature water and held under with a weighted gratefor four hours, then removed, patted dry, and weighed to determine themass of water accumulated by each square. Each square was examinedvisually for adhesive failure of the coating, as detected by peeling orpulling away of the coating from the cardboard. Hydrogenated heat bodiedlinseed oil (OKO M 2½) having an IV of 31.6 was also used as a boxcoating without any basestock petroleum wax. The wax pick-up was 2.1734grams, and water pick-up was very low (0.0819 grams). The wax pick-upand water pick-up results are presented in Table 4.

TABLE 4 Cardboard Coating Comparison: Petroleum Wax (Control) andPetroleum Wax with 3% Hydrogenated OKO 2½ Additive. Wax Water Controlwax Control water pick-up (g) pick-up (g) pick-up (g) pick-up (g) withadditive with additive Citgo PM 1.0731 0.385 1.1098 0.377 Robwax23091.0773 0.359 1.0970 0.389 Parvan 1270 1.0895 0.415 0.8151 0.692 Calumet0.8183 0.362 0.8196 0.653 SC5717 Additive 2.1734 0.0819 only

Roughly comparable levels of wax pick-up were obtained with Citgo PM,Robwax 2309, and Calumet SC5717 with and without 3% hydrogenated OKO 2½added to the petroleum wax. Water pick-up was comparable for Citgo PMand Robwax 2309 with and without hydrogenated OKO 2½ additive, butincreased when the additive was used with Calumet SC5717. The wax pickupobtained with Parvan 1270 decreased when 3% hydrogenated OKO 2½ wasadded to the wax. However, water pick-up increased.

Example 28 Polyester Polymerization Reaction

This Example sets forth a representative polyester polymerizationreaction using hydrogenated and partially hydrogenated polymerizedvegetable oils. Partially hydrogenated polymerized vegetable oil havingat least two free hydroxyl groups is combined with a molar quantity ofdiisocyanate half the molarity of free hydroxyl groups in partiallyhydrogenated polymerized (blown) vegetable oil to make polyurethane asdescribed by Frisch (Fundamental Chemistry and Catalysis ofPolyurethanes, Frisch, K. C., in, Polyurethane Technology, Paul Bruins,editor, Interscience Publishers, N.Y., 1969, hereby incorporated byreference in its entirety). A sample of partially hydrogenatedpolymerized soybean oil having a hydroxyl value of 50 is combined with adiisocyanate at 100° C. to make branched polymers suitable for use infibers, hard and soft elastomers, coatings and adhesives, flexible andrigid foams, and thermoplastics and thermosetting plastics.

Example 29 Candle

In this Example, blends of the hydrogenated polymerized oil withpropylene glycol monoesters were used in place of petroleum-based waxesto make waxes suitable for use in candle compositions. A gel candle(container candle) and a harder wax candle were produced.

Hydrogenated head-bodied linseed oil (OKO M 2½, 50 g, ADM) was meltedand blended with propylene glycol monostearate (50 g, 90% monoester,Aldo-90 Lonza, Allendale, N.J.) to form a candle wax. The resultingcomposition was poured into a container having a wick for use as acontainer candle. The resulting candle had a smooth appearance withoutany noticeable crystalline structure. The candle was shelf stable,showing no cracking or discoloration after storage at room temperaturefor 1 year.

In another example, candle wax was prepared by melting kettleheat-bodied linseed oil (Alinco Q, ADM) which was poured into a candlemold having a wick. The material was allowed to cool and the candleremoved from the mold. The candle was shelf stable, showing no crackingor discoloration after storage at room temperature for 1 year.

In another example, kettle heat-bodied linseed oil (Alinco X, ADM) wasmelted and blended with melted partially hydrogenated soybean oil havingan IV of 21 to form a candle wax. The candle wax was poured into acandle mold having a wick. The material was allowed to cool and thecandle removed from the mold.

Example 30 Animal Feed Blocks and Particulate Feeds

In this Example, hydrogenated and partially hydrogenated polymerizedvegetable oil are used to replace petroleum-based ingredients in animalfeed blocks. In these commercial protein and mineral block applications,individual ingredients are blended in a ribbon mixer, with the blendedmixture pressed in a hydraulic press to produce a feed block that weighsbetween 20 and 40 pounds. The hydrogenated polymerized vegetable oilsallow for individual ingredients to adhere to one another and thefinished product to retain its physical integrity. A sample feed blockformulation for a protein containing block is presented in Tables 5 anda sample mineral block formulation is presented in Table 6.

TABLE 5 Protein Block Protein block ingredients Percentage Oilseed meal69 Salt 13 Monocalcium phosphate, 21% 5 Calcium carbonate, 38% 4Non-protein nitrogen 3 Polymerized soy oil, hydrogenated 2 Vitamin-tracemineral premix 4 Total 100

TABLE 6 Mineral Block Mineral block ingredients Percentage Monocalciumphosphate, 21% 30 Calcium carbonate, 38% 26 Salt 15 Defluorinatedphosphate, 18% 10 Molasses, cane 4 Magnesium oxide 4 Oilseed meal 5Polymerized soy oil, hydrogenated 1 Vitamin-trace mineral premix 5 Total100

In another Example of a specific agglomerated, loose mineralapplications, polymerized soy oil is used to agglomerate (bind)micronutrients (e.g., zinc, manganese, copper, cobalt) to achieve a moreuniform particle size of the finished mineral product when combined withmacro-ingredients (e.g., monocalcium phosphate, limestone, defluorinatedphosphate). Typically, the micronutrients and oil source are pre-blendedto achieve the initial agglomeration, with the agglomerate blended withthe macro-ingredients in a ribbon mixer to produce the final product. Asample formula is presented in Table 7.

TABLE 7 Particulate Animal Feed Ingredient Percentage Monocalciumphosphate, 21% 44 Limestone, coarse 30 Salt 10 Oilseed meal 4Defluorinated phosphate, coarse 4 Polymerized soy oil, hydrogenated 3Molasses, cane 2 Vitamin-trace mineral premix 3 Total 100

Feeding the developed products to ruminant animals and other grazinganimals results in feed consumption within the targeted intake ranges.

Example 30 Personal Care Products

In this Example, personal care product formulations will be developedwhere the hydrogenated polymerized vegetable oils will replacepetroleum-derived petrolatums. A hand cream is prepared where petrolatumis replaced with a hydrogenated polymerized vegetable oil.

Deodorization, substantially as set forth in Example 13, removes freefatty acids, which reduces irritation, itching or skin sensitization dueto the residual free fatty acid content. Deodorized polymerized oil issubstituted for petrolatum to yield a hand cream having the compositionas set forth in Table 8. The ingredients are mixed together andresulting cream may be used as a hand cream or moisturizing cream.

TABLE 8 Hand Cream Formulation 400 mL jar of Vitamin “A” cream (anybrand) 400 mL jar of Vitamin “E” cream (any brand) 155 gram tubepolysporin 2 tbsp deodorized hydrogenated soybean oil 4 tbsp baby oil

Having now fully described this invention, it will be understood tothose of ordinary skill in the art that the same can be performed withina wide and equivalent range of conditions, formulations, and otherparameters without affecting the scope of the invention or anyembodiment thereof. All patents, patent applications, and publicationscited herein are fully incorporated by reference herein in theirentirety.

1. A material comprising: a hydrogenated polymerized oil, wherein thematerial is one of a binder and a coating.
 2. The material of claim 1,wherein the material is a binder selected from the group consisting of ahot melt adhesive, a binder for a wood composite material, a binder fora feed block, a binder for an agricultural product, an asphalt binder,and a binder for a personal care product.
 3. The material of claim 2,wherein the binder is a hot melt adhesive comprising 40% to 50% byweight of the hydrogenated polymerized oil, and further comprises 40% to50% by weight of a hydrocarbon resin and 10% to 20% by weight of ahydrogenated vegetable oil.
 4. The material of claim 2, wherein thebinder is a binder for a wood composite material wherein thehydrogenated polymerized oil comprises a partially hydrogenatedpolymerized oil and forms a crosslinked polymer network upon oxidativecuring.
 5. The material of claim 4, wherein the binder further forms anat least partially moisture resistant layer on at least one surface ofthe wood composite material.
 6. The material of claim 2, wherein thebinder is a binder for a feed block, wherein the feed block furthercomprises at least one additional component selected from the groupconsisting of proteins, non-protein nitrogen sources, vitamins,minerals, palatability increasing agents, and agro-industrialby-products selected from the group consisting of tomato pulp, olivecake, date pulp, rice bran, vegetable meals, oilseed meals, animalproteins, grain co-products, molasses, poultry waste, fermentationco-products, plant botanical extracts, and combinations thereof, andwherein the feed block is at least partially moisture resistant.
 7. Thematerial of claim 2, wherein the binder is a binder for an agriculturalproduct selected from the group consisting of a pesticide, an herbicide,a fertilizer, and a rodenticide.
 8. The material of claim 2, wherein thebinder is an asphalt binder, wherein the asphalt binder comprisespartially hydrogenated polymerized oil and the asphalt binder undergoesan oxidative cure, and wherein the material increases at least one oftoughness, low temperature ductility, high temperature viscosity,fatigue cracking resistance, impact resistance, and aggregate adhesion.9. The material of claim 2, wherein, the binder is a binder for apersonal care product, wherein the hydrogenated polymerized oil replacesa petrolatum product.
 10. A material of claim 1, wherein the material isa coating selected from the group consisting of a coating for anagricultural product, a packaging coating, an edible food coating, and aconcrete mold release coating.
 11. The material of claim 10, wherein thecoating is a packaging coating further comprising an alkyl ester. 12.The material of claim 10, wherein the material is a flexible packagingcoating.
 13. The material of claim 10, wherein the coating is an ediblefood coating selected from the group consisting of a fruit coating, avegetable coating, and an animal feed coating.
 14. The material of claim13, wherein the coating is an animal feed coating on an animal feedcomprising an ingredient selected from the group consisting of animalproteins, animal fats, plant proteins, plant oils, non-protein nitrogensources, and combinations of any thereof, wherein an amount of theanimal feed passing at least partially intact through a rumen of aruminant is increased compared to an animal feed that is not coated withthe animal feed coating.
 15. The material of claim 10, wherein thecoating is a concrete mold release coating, the coating furthercomprising at least one component selected from the group consisting ofa vegetable oil, an alcohol, a fusel oil mixture, a lactate ester, afatty acid methyl ester, and a propylene glycol monoester.
 16. A polymercomposition comprising a partially hydrogenated polymerized oil, whereinat least one remaining carbon-carbon double bond has been converted toat least one epoxide.
 17. The polymer composition of claim 16, whereinat least one of the at least one epoxide has been reacted with at leastone nucleophile to form a ring opened product.
 18. The polymercomposition of claim 17, wherein the nucleophile is one of water andhydroxide ion and the at least one of the at least one epoxide has beenconverted to at least one vicinal diol.
 19. A material comprising: ahydrogenated polymerized oil; and at least one organic material, whereinthe organic material is selected from the group consisting of avegetable based material and a petroleum derived material.
 20. Thematerial of claim 19, wherein the at least one organic material is apetrochemical derived material selected from the group consisting of aparaffin, a microcrystalline wax, a mineral oil, and combinations of anythereof.
 21. The material of claim 20, wherein the material is acoating.
 22. A grease comprising: a hydrogenated polymerized oil; and atleast one metal salt of a free fatty acid.
 23. An emulsion comprising: ahydrogenated polymerized oil; and at least one emulsifier selected fromthe group consisting of xanthum gum, propylene glycol alginate, locustbean gum, maltodextrin, a fatty alcolhol ethoxylate, a fatty acidethoxylate, a sorbitan derivative, a polyglycerol ester, lecithin, andcombinations of any thereof